Co-reporter:Yuanhao Wang;Yuanhe Li;Yijun Fan;Zhiguo Wang
Chemical Communications 2017 vol. 53(Issue 87) pp:11873-11876
Publication Date(Web):2017/10/31
DOI:10.1039/C7CC07543J
Pd-Catalyzed denitrogenative functionalizations of benzotriazoles with alkenes and 1,3-dienes have been developed, which enable the rapid access of diverse ortho-amino styrenes and 2-vinylindolines, respectively. This study shows the great potential of benzotriazoles as a [1C]-synthon in cross-coupling reactions and an aza-[3C]-synthon in cycloaddition reactions.
Co-reporter:Juan Feng;Xiaoqiang Lei;Ruiyang Bao;Yuanhe Li;Dr. Chengqian Xiao; Dr. Lihong Hu; Dr. Yefeng Tang
Angewandte Chemie 2017 Volume 129(Issue 51) pp:16541-16545
Publication Date(Web):2017/12/18
DOI:10.1002/ange.201710846
AbstractAn enantioselective synthesis of (+)-8-epi-xanthatin hinging on a chiral phosphoric acid catalyzed tandem allylboration/lactonization reaction is reported. With (+)-8-epi-xanthatin as the precursor, the collective synthesis of a series of synthetically challenging xanthanolides was also accomplished. Among them, xanthipungolide, one of the most complex xanthanolide monomers, was accessed through a bioinspired tandem double-bond isomerization/6π electronic cyclization/intramolecular Diels–Alder reaction, and pungiolides A, B, D, E, and L–N, a group of xanthanolide dimers, were assembled through a bioinspired Diels–Alder dimerization followed by late-stage diversification.
Co-reporter:Juan Feng;Xiaoqiang Lei;Zhen Guo; Yefeng Tang
Angewandte Chemie 2017 Volume 129(Issue 27) pp:8003-8007
Publication Date(Web):2017/06/26
DOI:10.1002/ange.201702893
AbstractWe report the concise total synthesis of homodimericin A (1), a recently identified fungal metabolite bearing an unprecedented molecular architecture. The success of the approach hinges on a series of rationally designed and bioinspired transformations, including a Moore rearrangement to assemble the monomeric hydroquinone precursor, homodimerization through double Michael addition to construct the planar A/B/C tricyclic framework, and a tandem Diels–Alder reaction/carbonyl–ene cyclization to forge the congested D/E/F tricyclic cage motif. Unequivocal evidence for the elucidated structure of homodimericin A was also provided by this study.
Co-reporter:Juan Feng;Xiaoqiang Lei;Ruiyang Bao;Yuanhe Li;Dr. Chengqian Xiao; Dr. Lihong Hu; Dr. Yefeng Tang
Angewandte Chemie International Edition 2017 Volume 56(Issue 51) pp:16323-16327
Publication Date(Web):2017/12/18
DOI:10.1002/anie.201710846
AbstractAn enantioselective synthesis of (+)-8-epi-xanthatin hinging on a chiral phosphoric acid catalyzed tandem allylboration/lactonization reaction is reported. With (+)-8-epi-xanthatin as the precursor, the collective synthesis of a series of synthetically challenging xanthanolides was also accomplished. Among them, xanthipungolide, one of the most complex xanthanolide monomers, was accessed through a bioinspired tandem double-bond isomerization/6π electronic cyclization/intramolecular Diels–Alder reaction, and pungiolides A, B, D, E, and L–N, a group of xanthanolide dimers, were assembled through a bioinspired Diels–Alder dimerization followed by late-stage diversification.
Co-reporter:Juan Feng;Xiaoqiang Lei;Zhen Guo; Yefeng Tang
Angewandte Chemie International Edition 2017 Volume 56(Issue 27) pp:7895-7899
Publication Date(Web):2017/06/26
DOI:10.1002/anie.201702893
AbstractWe report the concise total synthesis of homodimericin A (1), a recently identified fungal metabolite bearing an unprecedented molecular architecture. The success of the approach hinges on a series of rationally designed and bioinspired transformations, including a Moore rearrangement to assemble the monomeric hydroquinone precursor, homodimerization through double Michael addition to construct the planar A/B/C tricyclic framework, and a tandem Diels–Alder reaction/carbonyl–ene cyclization to forge the congested D/E/F tricyclic cage motif. Unequivocal evidence for the elucidated structure of homodimericin A was also provided by this study.
Co-reporter:Yuanhao Wang;Yunfei Wu;Yuanhe Li
Chemical Science (2010-Present) 2017 vol. 8(Issue 5) pp:3852-3857
Publication Date(Web):2017/05/03
DOI:10.1039/C7SC00367F
Unprecedented palladium-catalyzed denitrogenative Suzuki and carbonylative Suzuki coupling reactions of benzotriazoles with boronic acids have been realized, which afforded structurally diverse ortho-amino-substituted biaryl and biaryl ketone derivatives. The key to this success is due to the development of a rationally designed strategy to achieve the ring opening of benzotriazoles with a synergistic activating–stabilizing effect, which enables the in situ generation of the corresponding ortho-amino-arenediazonium species. The present work opens up a new avenue to utilize benzotriazoles as synthetic equivalents of ortho-amino-arenediazoniums, which otherwise could not be directly accessed by existing synthetic methods.
Co-reporter:Xiaoqiang Lei, Mohan Gao, and Yefeng Tang
Organic Letters 2016 Volume 18(Issue 19) pp:4990-4993
Publication Date(Web):September 27, 2016
DOI:10.1021/acs.orglett.6b02454
A Rh(II)-catalyzed transannulation of N-sulfonyl-1,2,3-triazoles with 2,1-benzisoxazoles has been developed, which affords an efficient method for the synthesis of quinazoline derivatives. The transformation represents an unprecedented example which utilizes N-sulfonyl-1,2,3-triazole as an aza-[2C]-component in cycloadditions. Meanwhile, a Rh(II)-catalyzed formal [3 + 2] cycloaddition of N-sulfonyl-1,2,3-triazoles with 1,2-benzisoxazoles is also presented, which enables the rapid synthesis of functionalized imidazole derivatives.
Co-reporter:Hongzhi Yang, Xue Liu, Qingong Li, Longbo Li, Jing-Ren Zhang and Yefeng Tang
Organic & Biomolecular Chemistry 2016 vol. 14(Issue 1) pp:198-205
Publication Date(Web):14 Oct 2015
DOI:10.1039/C5OB01946J
A modular synthesis of merochlorins A and B, two naturally occurring antibiotics, has been achieved concisely from readily available building blocks in 4–6 steps. The key steps include the bio-inspired tandem phenol oxidative dearomatization/[5 + 2] and [3 + 2] cycloadditions to construct the tricyclic cores of the targets, and the intermolecular Diels–Alder reaction followed by dehydrogenative aromatization to assemble the remaining aromatic units. The antibacterial activities of merochlorins A, B and some advanced synthetic intermediates were also evaluated, which provided valuable information on the structure–activity relationship (SAR) of this class of new antibiotics.
Co-reporter:Hongzhi Yang, Juan Feng, Yuanhe Li, and Yefeng Tang
Organic Letters 2015 Volume 17(Issue 6) pp:1441-1444
Publication Date(Web):February 27, 2015
DOI:10.1021/acs.orglett.5b00321
The first total syntheses of rubialatins A and B, two newly discovered naphthohydroquinone dimers, were achieved with high efficiency and elegancy through rationally designed biomimetic approaches. The tandem ring contraction/Michael addition/aldol reaction followed by oxidation enabled the rapid access of prerubialatin from readily available precursors, which then diverted into rubialatins A and B via epoxidation and photoinduced skeletal rearrangement, respectively. Moreover, several new rubialatin congeners were also obtained along the synthetic tour, some of which were proved to be authentic natural products.
Co-reporter:Yuanhao Wang, Xiaoqiang Lei and Yefeng Tang
Chemical Communications 2015 vol. 51(Issue 21) pp:4507-4510
Publication Date(Web):09 Feb 2015
DOI:10.1039/C5CC00268K
The Rh(II)-catalyzed formal [3+2] and [3+3] cycloadditions of 1-tosyl 1,2,3-triazoles with 2H-azirines have been developed, which enable the efficient synthesis of polysubstituted 3-aminopyrroles and 1,2-dihydropyrazines, respectively. The reported [3+2] cycloaddition represents the first application of 1-sulfonyl 1,2,3-triazole as a [2C]-component in relevant cycloaddition reactions.
Co-reporter:Yu Tian, Yuanhao Wang, Hai Shang, Xudong Xu and Yefeng Tang
Organic & Biomolecular Chemistry 2015 vol. 13(Issue 2) pp:612-619
Publication Date(Web):30 Oct 2014
DOI:10.1039/C4OB01910E
Rhodium(II)-catalyzed intramolecular [4 + 3] cycloadditions of dienyltriazoles have been developed, which enable the efficient synthesis of various fused 2,5-dihydroazepines. Mechanistically, the titled reaction proceeds via an interesting tandem cyclopropanation/aza-cope rearrangement.
Co-reporter:Huan Wang, Shuo Wang, Lili Cheng, Ligong Chen, Yongguang Wang, Jie Qing, Shengdian Huang, Yuanhao Wang, Xiaoqiang Lei, Yunfei Wu, Zhilong Ma, Linqi Zhang, and Yefeng Tang
ACS Medicinal Chemistry Letters 2015 Volume 6(Issue 9) pp:977
Publication Date(Web):July 27, 2015
DOI:10.1021/acsmedchemlett.5b00159
RO8191 represents a newly discovered small-molecule IFN-like agent that displays potent anti-HCV activity. With it as lead, a series of compounds bearing an imidazo[1,2-α][1,8]naphthyridine core and an amide bond-linked side chain were designed and synthesized. These compounds were evaluated on HCV cell culture system (HCVcc-hRluc-JFH1), and some of them exhibited remarkable anti-HCV activity (EC50 = 0.017–0.159 μM) and low toxicity (CC50 > 25 μM). Moreover, it was revealed that these newly identified anti-HCV agents exert their antiviral effect through a distinct mechanism of action from that of RO8191 by targeting the viral entry process. Thus, our study provides a starting point for the development of potential HCV entry inhibitor.Keywords: anti-HCV agent; entry inhibitor; Hepatitis C virus; IFN-like compound; RO8191
Co-reporter:Shengdian Huang, Jie Qing, Shuo Wang, Huan Wang, Linqi Zhang and Yefeng Tang
Organic & Biomolecular Chemistry 2014 vol. 12(Issue 15) pp:2344-2348
Publication Date(Web):28 Jan 2014
DOI:10.1039/C3OB42525H
RO8191 represents a newly identified small-molecule IFN-α-substitute, which displays potent anti-HCV activity. In this communication, we reported the design and synthesis of two series of imidazo[1,2-α][1,8]naphthyridine derivatives, as RO8191 analogues, via a direct C–H arylation approach. Notably, by adjusting the reaction conditions, we could achieve the two series of analogues via regioselective single- and double-arylations, respectively. The anti-HCV activities of the synthesized compounds were evaluated within the HCV cell culture system, and the preliminary results showed that some of them displayed promising anti-HCV activities.
Co-reporter:Juan Feng, Yuanhao Wang, Qingong Li, Renwang Jiang, Yefeng Tang
Tetrahedron Letters 2014 Volume 55(Issue 47) pp:6455-6458
Publication Date(Web):19 November 2014
DOI:10.1016/j.tetlet.2014.09.134
A novel Rh(II)-catalyzed transannulation of 1-tosyl-1,2,3-triazoles with silyl or alkyl enol ethers has been developed, which enables the facile synthesis of substituted pyrroles in a regiocontrollable manner. Moreover, the methodology could be extended to access 3-pyrrolin-2-one derivatives with silyl ketene acetals used as the reaction partner.
Co-reporter:Dr. Hai Shang;Dr. Junhua Liu;Ruiyang Bao;Dr. Yu Cao;Kun Zhao;Chengqian Xiao;Dr. Bing Zhou;Dr. Lihong Hu;Dr. Yefeng Tang
Angewandte Chemie 2014 Volume 126( Issue 52) pp:14722-14726
Publication Date(Web):
DOI:10.1002/ange.201406461
Abstract
Starting from xanthatin, the biomimetic synthesis of 4β,5β-epoxyxanthatin-1α,4α-endoperoxide, a novel monomeric xanthanolide, has been achieved. Moreover, four unprecedented xanthanolide dimers were synthesized by three different dimerizations of xanthatin, either in a head-to-head or head-to-tail fashion. Notably, these dimeric compounds were firstly identified as artifacts in the laboratory, and two of them, mogolides A and B, proved to be natural products present in the Xanthium mogolium Kitag plant.
Co-reporter:Dr. Hai Shang;Dr. Junhua Liu;Ruiyang Bao;Dr. Yu Cao;Kun Zhao;Chengqian Xiao;Dr. Bing Zhou;Dr. Lihong Hu;Dr. Yefeng Tang
Angewandte Chemie International Edition 2014 Volume 53( Issue 52) pp:14494-14498
Publication Date(Web):
DOI:10.1002/anie.201406461
Abstract
Starting from xanthatin, the biomimetic synthesis of 4β,5β-epoxyxanthatin-1α,4α-endoperoxide, a novel monomeric xanthanolide, has been achieved. Moreover, four unprecedented xanthanolide dimers were synthesized by three different dimerizations of xanthatin, either in a head-to-head or head-to-tail fashion. Notably, these dimeric compounds were firstly identified as artifacts in the laboratory, and two of them, mogolides A and B, proved to be natural products present in the Xanthium mogolium Kitag plant.
Co-reporter:Dr. Hai Shang;Yuanhao Wang;Dr. Yu Tian;Juan Feng;Dr. Yefeng Tang
Angewandte Chemie 2014 Volume 126( Issue 22) pp:5768-5772
Publication Date(Web):
DOI:10.1002/ange.201400426
Abstract
The first rhodium(II)-catalyzed aza-[4+3] cycloadditions of 1-sulfonyl 1,2,3-triazoles with 1,3-dienes have been developed, and enable the efficient synthesis of highly functionalized 2,5-dihydroazepines from readily available precursors. In some cases, the reaction pathway could divert to formal aza-[3+2] cycloadditions, thus leading to 2,3-dihydropyrroles. In this context, the titled reaction represents a capable tool for the divergent synthesis of two types of synthetically valuable aza-heterocycles from common rhodium(II) iminocarbene intermediates.
Co-reporter:Dr. Hai Shang;Yuanhao Wang;Dr. Yu Tian;Juan Feng;Dr. Yefeng Tang
Angewandte Chemie International Edition 2014 Volume 53( Issue 22) pp:5662-5666
Publication Date(Web):
DOI:10.1002/anie.201400426
Abstract
The first rhodium(II)-catalyzed aza-[4+3] cycloadditions of 1-sulfonyl 1,2,3-triazoles with 1,3-dienes have been developed, and enable the efficient synthesis of highly functionalized 2,5-dihydroazepines from readily available precursors. In some cases, the reaction pathway could divert to formal aza-[3+2] cycloadditions, thus leading to 2,3-dihydropyrroles. In this context, the titled reaction represents a capable tool for the divergent synthesis of two types of synthetically valuable aza-heterocycles from common rhodium(II) iminocarbene intermediates.
Co-reporter:Hongzhi Yang, Juan Feng and Yefeng Tang
Chemical Communications 2013 vol. 49(Issue 57) pp:6442-6444
Publication Date(Web):30 May 2013
DOI:10.1039/C3CC42686F
The first total syntheses of spirobacillenes A and B were achieved concisely. The key transformation leading to spirobacillene A features a biomimetic intramolecular phenol–enol oxidative coupling reaction, and that leading to spirobacillene B highlights a bio-inspired intramolecular indole–ketone enolate oxidative coupling reaction.
Co-reporter:Zhaofeng Wang, Kun Zhao, Junkai Fu, Junlin Zhang, Weiyu Yin and Yefeng Tang
Organic & Biomolecular Chemistry 2013 vol. 11(Issue 13) pp:2093-2097
Publication Date(Web):11 Feb 2013
DOI:10.1039/C3OB00046J
The organocatalytic additions of ascorbic acid to various α,β-unsaturated aldehydes via tandem 1,4-conjugate addition/hemiacetalization/hemiketalization were developed, which provided a rapid entry into the 5-5-5 spirodilactone cores of a family of ascorbylated natural products. Based on the described chemistry, total syntheses of leucodrin, leudrin and the proposed structure of dilaspirolactone were achieved.
Co-reporter:Yue-Jie Chen, Rui-Yang Bao, Xiao-Dong Zhang, Ye-Feng Tang
Chinese Chemical Letters 2013 Volume 24(Issue 11) pp:953-956
Publication Date(Web):November 2013
DOI:10.1016/j.cclet.2013.07.015
An efficient formal synthesis of (+)-tashiromine was achieved by employing an intermolecular asymmetric Mannich-type reaction as the key step. Concurrently, a novel approach toward the total synthesis of (+)-stemoamide through dyotropic rearrangement of 3,4-cis-β-lactone was also explored.A formal synthesis of (+)-tashiromine was achieved concisely, and a novel synthetic approach toward (+)-stemoamide via dyotropic rearrangement of β-lactone was also explored.
Co-reporter:Junkai Fu;Dr. Hai Shang;Zhaofeng Wang;Dr. Le Chang;Wenbing Shao;Dr. Zhen Yang;Dr. Yefeng Tang
Angewandte Chemie International Edition 2013 Volume 52( Issue 15) pp:4198-4202
Publication Date(Web):
DOI:10.1002/anie.201208305
Co-reporter:Pengtao Zhang, Yongguang Wang, Ruiyang Bao, Tuoping Luo, Zhen Yang, and Yefeng Tang
Organic Letters 2012 Volume 14(Issue 1) pp:162-165
Publication Date(Web):December 13, 2011
DOI:10.1021/ol2029433
Enantioselective total syntheses of katsumadain and katsumadain C were achieved concisely through a biomimetic approach. Assembly of styryl-2-pyranone (3) and monoterpene 6 via acid-promoted regio- and stereoselective C–C bond formation afforded katsumadain (2), which underwent the photoinduced [2 + 2] dimerization in a head-to-tail mode to furnish katsumadain C (1).
Co-reporter:Kun Zhao, Gui-Juan Cheng, Hongzhi Yang, Hai Shang, Xinhao Zhang, Yun-Dong Wu, and Yefeng Tang
Organic Letters 2012 Volume 14(Issue 18) pp:4878-4881
Publication Date(Web):September 4, 2012
DOI:10.1021/ol302205w
A concise biomimetic total synthesis of incarvilleatone and incarviditone is achieved in one pot via the highly stereoselective hetero- and homodimerization of (±)-rengyolone, respectively. The structure of incarviditone is revised on the basis of spectroscopic and computational evidence.
Co-reporter:Dr. Weiwu Ren;Yichao Bian;Ziyang Zhang;Dr. Hai Shang;Pengtao Zhang;Yuejie Chen;Dr. Zhen Yang;Dr. Tuoping Luo;Dr. Yefeng Tang
Angewandte Chemie International Edition 2012 Volume 51( Issue 28) pp:6984-6988
Publication Date(Web):
DOI:10.1002/anie.201202643
Co-reporter:Dr. Weiwu Ren;Yichao Bian;Ziyang Zhang;Dr. Hai Shang;Pengtao Zhang;Yuejie Chen;Dr. Zhen Yang;Dr. Tuoping Luo;Dr. Yefeng Tang
Angewandte Chemie 2012 Volume 124( Issue 28) pp:7090-7094
Publication Date(Web):
DOI:10.1002/ange.201202643
Co-reporter:Ziyang Zhang, Jiahua Chen, Zhen Yang, and Yefeng Tang
Organic Letters 2010 Volume 12(Issue 23) pp:5554-5557
Publication Date(Web):November 9, 2010
DOI:10.1021/ol102438r
A biomimetic total synthesis of (±)-rossinone B has been achieved through a highly efficient strategy featuring a series of rationally designed reactions, including a one-pot allylic rearrangement/oxidation reaction to generate the vinyl quinone 27, an intramolecular vinyl quinone Diels−Alder reaction to construct the linear 6−6−5 tricyclic core of 28, and a double conjugate addition/β-elimination cascade to complete the total synthesis of 1.
Co-reporter:Xiaoqiang Lei; Longbo Li; Yu-Peng He
Organic Letters () pp:
Publication Date(Web):October 15, 2015
DOI:10.1021/acs.orglett.5b02570
A novel rhodium(II)-catalyzed formal [3 + 2] cycloaddition of N-sulfonyl-1,2,3-triazoles with isoxazoles has been achieved that provides an efficient method for the synthesis of polysubstituted 3-aminopyrrole derivatives. An operationally simple one-pot synthesis of the titled compounds from terminal alkynes, tosyl azide, and isoxazoles was also developed. The presented reaction affords an illustrative example of employing 1,2,3-triazoles as the [2C]-component in relevant cycloaddition reactions.
Co-reporter:Zhaofeng Wang, Kun Zhao, Junkai Fu, Junlin Zhang, Weiyu Yin and Yefeng Tang
Organic & Biomolecular Chemistry 2013 - vol. 11(Issue 13) pp:NaN2097-2097
Publication Date(Web):2013/02/11
DOI:10.1039/C3OB00046J
The organocatalytic additions of ascorbic acid to various α,β-unsaturated aldehydes via tandem 1,4-conjugate addition/hemiacetalization/hemiketalization were developed, which provided a rapid entry into the 5-5-5 spirodilactone cores of a family of ascorbylated natural products. Based on the described chemistry, total syntheses of leucodrin, leudrin and the proposed structure of dilaspirolactone were achieved.
Co-reporter:Shengdian Huang, Jie Qing, Shuo Wang, Huan Wang, Linqi Zhang and Yefeng Tang
Organic & Biomolecular Chemistry 2014 - vol. 12(Issue 15) pp:NaN2348-2348
Publication Date(Web):2014/01/28
DOI:10.1039/C3OB42525H
RO8191 represents a newly identified small-molecule IFN-α-substitute, which displays potent anti-HCV activity. In this communication, we reported the design and synthesis of two series of imidazo[1,2-α][1,8]naphthyridine derivatives, as RO8191 analogues, via a direct C–H arylation approach. Notably, by adjusting the reaction conditions, we could achieve the two series of analogues via regioselective single- and double-arylations, respectively. The anti-HCV activities of the synthesized compounds were evaluated within the HCV cell culture system, and the preliminary results showed that some of them displayed promising anti-HCV activities.
Co-reporter:Yuanhao Wang, Xiaoqiang Lei and Yefeng Tang
Chemical Communications 2015 - vol. 51(Issue 21) pp:NaN4510-4510
Publication Date(Web):2015/02/09
DOI:10.1039/C5CC00268K
The Rh(II)-catalyzed formal [3+2] and [3+3] cycloadditions of 1-tosyl 1,2,3-triazoles with 2H-azirines have been developed, which enable the efficient synthesis of polysubstituted 3-aminopyrroles and 1,2-dihydropyrazines, respectively. The reported [3+2] cycloaddition represents the first application of 1-sulfonyl 1,2,3-triazole as a [2C]-component in relevant cycloaddition reactions.
Co-reporter:Yuanhao Wang, Yunfei Wu, Yuanhe Li and Yefeng Tang
Chemical Science (2010-Present) 2017 - vol. 8(Issue 5) pp:
Publication Date(Web):
DOI:10.1039/C7SC00367F
Co-reporter:Yu Tian, Yuanhao Wang, Hai Shang, Xudong Xu and Yefeng Tang
Organic & Biomolecular Chemistry 2015 - vol. 13(Issue 2) pp:NaN619-619
Publication Date(Web):2014/10/30
DOI:10.1039/C4OB01910E
Rhodium(II)-catalyzed intramolecular [4 + 3] cycloadditions of dienyltriazoles have been developed, which enable the efficient synthesis of various fused 2,5-dihydroazepines. Mechanistically, the titled reaction proceeds via an interesting tandem cyclopropanation/aza-cope rearrangement.
Co-reporter:Hongzhi Yang, Juan Feng and Yefeng Tang
Chemical Communications 2013 - vol. 49(Issue 57) pp:NaN6444-6444
Publication Date(Web):2013/05/30
DOI:10.1039/C3CC42686F
The first total syntheses of spirobacillenes A and B were achieved concisely. The key transformation leading to spirobacillene A features a biomimetic intramolecular phenol–enol oxidative coupling reaction, and that leading to spirobacillene B highlights a bio-inspired intramolecular indole–ketone enolate oxidative coupling reaction.
Co-reporter:Hongzhi Yang, Xue Liu, Qingong Li, Longbo Li, Jing-Ren Zhang and Yefeng Tang
Organic & Biomolecular Chemistry 2016 - vol. 14(Issue 1) pp:NaN205-205
Publication Date(Web):2015/10/14
DOI:10.1039/C5OB01946J
A modular synthesis of merochlorins A and B, two naturally occurring antibiotics, has been achieved concisely from readily available building blocks in 4–6 steps. The key steps include the bio-inspired tandem phenol oxidative dearomatization/[5 + 2] and [3 + 2] cycloadditions to construct the tricyclic cores of the targets, and the intermolecular Diels–Alder reaction followed by dehydrogenative aromatization to assemble the remaining aromatic units. The antibacterial activities of merochlorins A, B and some advanced synthetic intermediates were also evaluated, which provided valuable information on the structure–activity relationship (SAR) of this class of new antibiotics.
![2-Propenoic acid, 2-[[tris(1-methylethyl)silyl]oxy]-, methyl ester](http://img.cochemist.com/ccimg/600200/600154-91-4.png)
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![1H-Pyrrole, 1-[(4-methylphenyl)sulfonyl]-3-phenyl-](http://img.cochemist.com/ccimg/153700/153633-35-3.png)
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![SILANE, (1,1-DIMETHYLETHYL)[[1-(4-METHOXYPHENYL)ETHENYL]OXY]DIMETHYL-](http://img.cochemist.com/ccimg/80700/80676-78-4_b.png)
![Silane, [[(1E)-1-ethoxy-1-propenyl]oxy]trimethyl-](http://img.cochemist.com/ccimg/74000/73967-97-2.png)
![Silane, [[(1E)-1-ethoxy-1-propenyl]oxy]trimethyl-](http://img.cochemist.com/ccimg/74000/73967-97-2_b.png)
![Silane, (1,1-dimethylethyl)dimethyl[(1-phenylethenyl)oxy]-](http://img.cochemist.com/ccimg/66400/66324-10-5.png)
![Silane, (1,1-dimethylethyl)dimethyl[(1-phenylethenyl)oxy]-](http://img.cochemist.com/ccimg/66400/66324-10-5_b.png)
![1H-Indole, 3-ethenyl-1-[(4-methylphenyl)sulfonyl]-](http://img.cochemist.com/ccimg/65100/65037-62-9.png)
![1H-Indole, 3-ethenyl-1-[(4-methylphenyl)sulfonyl]-](http://img.cochemist.com/ccimg/65100/65037-62-9_b.png)
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