Hongbin Zhai

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Name: 翟宏斌; HongBin Zhai

Organization: Lanzhou University

Department: The State Key Laboratory of Applied Organic Chemistry and School of Pharmacy

Title: Professor

Chemicals
References

First total synthesis of (−)-salprzelactone

Co-reporter:Bingzhen Ma, Hongyan Zheng, Yun Li, Hongjian Yang, Cheng Tao, Bin Cheng, Hongbin Zhai

Tetrahedron Letters 2017 Volume 58, Issue 18(Issue 18) pp:

Publication Date(Web):3 May 2017

DOI:10.1016/j.tetlet.2017.03.072

•First asymmetric total synthesis of salprzelactone and its C14 epimer have been achieved.•An intermolecular aldol condensation was used for the conjunction of the two fragments.•Step-economical and devoid of protecting group manipulations.The first enantioselective total synthesis of (−)-salprzelactone, a seco-norabietane diterpenoid has been accomplished in only three steps. Key transformations of the synthesis include an intermolecular aldol reaction and lactonization.Download high-res image (52KB)Download full-size image

An environmentally friendly approach to pyrrolo[1,2-a]quinoxalines using oxygen as the oxidant

Co-reporter:Chao Wang, Yun Li, Jianfei Zhao, Bin Cheng, Huifei Wang, Hongbin Zhai

Tetrahedron Letters 2016 Volume 57(Issue 35) pp:3908-3911

Publication Date(Web):31 August 2016

DOI:10.1016/j.tetlet.2016.07.041

•A mechanism for the transformation has been proposed.•One pot synthesis of pyrrolo[1,2-a]quinoxaline derivatives.•Catalyst and additive free protocol.We have developed an environmentally benign and practical protocol for the synthesis of pyrrolo[1,2-a]quinoxalines, which represent ubiquitous structural units common to a number of biologically active compounds. This synthetic system features simple operation and using clean oxidant, as well as mild reaction conditions. Both aromatic and aliphatic aldehydes can be used for the reaction and the products were obtained in good to excellent yields.

Synthesis of Polysubstituted Pyridines via a One-Pot Metal-Free Strategy

Co-reporter:Hongbo Wei, Yun Li, Ke Xiao, Bin Cheng, Huifei Wang, Lin Hu, and Hongbin Zhai

Organic Letters 2015 Volume 17(Issue 24) pp:5974-5977

Publication Date(Web):December 10, 2015

DOI:10.1021/acs.orglett.5b02903

An efficient strategy for the one-pot synthesis of polysubstituted pyridines via a cascade reaction from aldehydes, phosphorus ylides, and propargyl azide is reported. The reaction sequence involves a Wittig reaction, a Staudinger reaction, an aza-Wittig reaction, a 6π-3-azatriene electrocyclization, and a 1,3-H shift. This protocol provides quick access to the polysubstituted pyridines from readily available substrates in good to excellent yields.

Iodine-Catalyzed Facile Synthesis of Pyrrolo- and Indolo[1,2-a]quinoxalines

Co-reporter:Chao Wang;Yun Li;Rui Guo;Jingjing Tian;Cheng Tao;Bin Cheng;Hongyu Wang;Jun Zhang;Dr. Hongbin Zhai

Asian Journal of Organic Chemistry 2015 Volume 4( Issue 9) pp:866-869

Publication Date(Web):

DOI:10.1002/ajoc.201500174

Abstract

A practical and green approach to pyrrolo- and indolo[1,2-a]quinoxalines has been developed based upon an oxidative reaction of 1-(2-aminophenyl)pyrroles or 2-(3-methyl-1H-1-indolyl)aniline with benzylamines in the presence of O₂ as the environmentally friendly oxidant and iodine as an economical and effective catalyst.

Expedient Construction of the [5-6-7] Tricyclic Core of Calyciphylline A-Type Alkaloids

Co-reporter:Jing-Jing Guo;Dr. Yun Li;Dr. Bin Cheng;Tingting Xu;Cheng Tao;Xinkan Yang;Denghong Zhang;Guangqi Yan;Dr. Hongbin Zhai

Chemistry – An Asian Journal 2015 Volume 10( Issue 4) pp:865-868

Publication Date(Web):

DOI:10.1002/asia.201403061

Abstract

An efficient synthetic route toward the highly congested [5-6-7] tricyclic core of calyciphylline A-type alkaloids has been developed. This approach features a highly efficient intramolecular Diels–Alder cycloaddition to establish the aza-five-membered C ring as well as the C1 all-carbon quaternary center, and a subsequent cyclopropanation together with a ring-expansion reaction of the resulted adduct to construct the seven-membered D ring.

Silver(I)-Catalyzed Ring-Contractive Rearrangement: A New Entry to 5-Alkylidene-2-cyclopentenones

Co-reporter:Liang Zhao, Jinlian Wang, Hongyan Zheng, Yun Li, Ke Yang, Bin Cheng, Xiaojie Jin, Xiaojun Yao, and Hongbin Zhai

Organic Letters 2014 Volume 16(Issue 24) pp:6378-6381

Publication Date(Web):December 1, 2014

DOI:10.1021/ol503176y

A novel silver(I)-catalyzed ring-contractive rearrangement of 5-substituted 6-diazo-2-cyclohexenones has been developed, providing a new and efficient access to 5-alkylidene-2-cyclopentenones. The AgOTf-catalyzed reaction proceeds through metal–carbenoid formation followed by endocyclic allyl [1,2] migration with excellent stereoselectivity and broad substrate scope.

Total Synthesis of Indole Alkaloid (±)-Subincanadine E

Co-reporter:Jingjing Tian, Qiuchen Du, Rui Guo, Yun Li, Bin Cheng, and Hongbin Zhai

Organic Letters 2014 Volume 16(Issue 12) pp:3173-3175

Publication Date(Web):May 28, 2014

DOI:10.1021/ol501308p

The first total synthesis of indole alkaloid (±)-subincanadine E has been accomplished. Ni(COD)2-mediated intramolecular Michael addition and zinc-mediated fragmentation reaction served as two key transformations.

Total Synthesis of (±)-Sculponeatin N

Co-reporter:Zhiqiang Pan, Cunying Zheng, Hongyu Wang, Yanhe Chen, Yun Li, Bin Cheng, and Hongbin Zhai

Organic Letters 2014 Volume 16(Issue 1) pp:216-219

Publication Date(Web):December 2, 2013

DOI:10.1021/ol403208g

The first total synthesis of the (±)-sculponeatin N (a 6,7-seco-ent-kaurane diterpenoid discovered by Sun and co-workers) has been achieved. The features include a regio- and stereoselective aldol reaction to form a lactone, an intramolecular Diels–Alder reaction to install B and C rings simultaneously, and a radical cyclization to forge the D ring.

Stereocontrolled Total Syntheses of (±)-Fawcettimine, (±)-Lycoflexine, and (±)-Lycoflexine N-Oxide

Co-reporter:Ke Xu, Bin Cheng, Yun Li, Tingting Xu, Cunming Yu, Jun Zhang, Zhiqiang Ma, and Hongbin Zhai

Organic Letters 2014 Volume 16(Issue 1) pp:196-199

Publication Date(Web):December 2, 2013

DOI:10.1021/ol403185g

New stereocontrolled total syntheses of (±)-fawcettimine, (±)-lycoflexine, and (±)-lycoflexine N-oxide have been accomplished. The highlights include a one-pot annulation to construct the enedione and a microwave-promoted Diels–Alder reaction.

Synthetic Studies Toward Harringtonolide

Co-reporter:Dr. Zhiqiang Ma;Dr. Bin Cheng;Dr. Hongbin Zhai

Asian Journal of Organic Chemistry 2014 Volume 3( Issue 10) pp:1097-1101

Publication Date(Web):

DOI:10.1002/ajoc.201402116

Abstract

An efficient synthesis of an oxo-bridged 7/6-bicyclic precursor that is potentially useful for the construction of harringtonolide has been realized through a [4+3] cycloaddition reaction. Meanwhile, an unexpected rearrangement reaction, which could be used for the fast assembly of spirocycles, was found during the double elimination attempts.

Facile Synthesis of 2-Arylphenols via Palladium-Catalyzed Cross-Coupling of Aryl Iodides with 6-Diazo-2-cyclohexenones

Co-reporter:Ke Yang, Jun Zhang, Yun Li, Bin Cheng, Liang Zhao, and Hongbin Zhai

Organic Letters 2013 Volume 15(Issue 4) pp:808-811

Publication Date(Web):January 30, 2013

DOI:10.1021/ol303484f

2-Arylphenols were conveniently synthesized from aryl iodides and 6-diazo-2-cyclohexenones, in moderate to excellent yields, via tandem Pd-catalyzed cross-coupling/aromatization. The preliminary results for the corresponding enantioselective version showed that the coupling products could be generated in up to 72% ee.

Direct Access to Tetrahydro[1,2]diazepinones from α,β-Epoxy-N-aziridinylimines via Anionic Rearrangement

Co-reporter:Fufang Wu, Min Dong, Fang Fang, Yingxia Sang, Yun Li, Bin Cheng, Lihe Zhang, and Hongbin Zhai

Organic Letters 2013 Volume 15(Issue 4) pp:914-916

Publication Date(Web):February 4, 2013

DOI:10.1021/ol400070j

A novel one-step synthetic approach to tetrahydro[1,2]diazepinones via base-promoted rearrangement of α,β-epoxy-N-aziridinylimines, derived from α,β-epoxyketones and N-aminoaziridines, has been developed.

Synthesis of the Tetracyclic Core Structure of ()-NakadomarinA through Azomethine Ylide-Alkene [3+2] Cycloaddtion

Co-reporter:Dr. Fufang Wu;Yanhe Chen;Dr. Bin Cheng;Dr. Yun Li;Dr. Hongbin Zhai

Asian Journal of Organic Chemistry 2013 Volume 2( Issue 7) pp:561-564

Publication Date(Web):

DOI:10.1002/ajoc.201300100

Total Synthesis of ()-Jiadifenin

Co-reporter:Dr. Yang Yang;Dr. Xingnian Fu;Dr. Jianwei Chen;Dr. Hongbin Zhai

Angewandte Chemie 2012 Volume 124( Issue 39) pp:9963-9966

Publication Date(Web):

DOI:10.1002/ange.201203176

Total Synthesis of ()-Jiadifenin

Co-reporter:Dr. Yang Yang;Dr. Xingnian Fu;Dr. Jianwei Chen;Dr. Hongbin Zhai

Angewandte Chemie International Edition 2012 Volume 51( Issue 39) pp:9825-9828

Publication Date(Web):

DOI:10.1002/anie.201203176

One-Step Construction of Tetrahydro-5H-indolo[3,2-c]quinolines from Benzyl Azides and Indoles via a Cascade Reaction Sequence

Co-reporter:Zengqiang Song, Yu-Ming Zhao, and Hongbin Zhai

Organic Letters 2011 Volume 13(Issue 24) pp:6331-6333

Publication Date(Web):November 10, 2011

DOI:10.1021/ol202656u

A novel one-step assembly of tetrahydro-5H-indolo[3,2-c]quinolines from benzyl azides and indoles via a formal [4 + 2] cycloaddition is described. A cascade reaction sequence, which involves benzyl azide-to-iminium rearrangement followed by two sequential Pictet–Spengler reactions, generates the tetracycles in moderate to excellent yields. The current method is applicable to a broad substrate scope and holds significant potential in constructing polycyclic indolines with tertiary and/or quaternary carbon centers.

Fast and Protecting-Group-Free Synthesis of (±)-Subincanadine C

Co-reporter:Fangmiao Yu, Bin Cheng, and Hongbin Zhai

Organic Letters 2011 Volume 13(Issue 21) pp:5782-5783

Publication Date(Web):October 4, 2011

DOI:10.1021/ol202349g

The first total synthesis of (±)-subincanadine C has been accomplished in a protecting-group-free fashion. This pentacyclic indole alkaloid was synthesized in six steps from the known intermediate 4, featuring Ni(COD)2-mediated intramolecular Michael addition as a key transformation.

Concise Synthesis of the Oxapentacyclic Core of Cortistatin A

Co-reporter:Fangmiao Yu, Guozhi Li, Peng Gao, Hongju Gong, Yinghua Liu, Yongming Wu, Bin Cheng, and Hongbin Zhai

Organic Letters 2010 Volume 12(Issue 22) pp:5135-5137

Publication Date(Web):October 6, 2010

DOI:10.1021/ol102058f

A concise synthetic approach for constructing the oxapentacyclic framework of cortistatin A is described. The synthesis features a furan−oxyallyl [4 + 3] cycloaddition and double-intramolecular aldol reactions. In addition, an interesting core structure was obtained in 11 steps from furan by using our method.

Stereoselective Synthesis of (2Z)-2,4-Dienamides via NBS-Mediated Allyloxyl Addition–Claisen Rearrangement–Dehydrobromination Cascade Reaction of Ynsulfonamides

Co-reporter:Runbo Ding; Yun Li; Cheng Tao; Bin Cheng

Organic Letters () pp:

Publication Date(Web):August 13, 2015

DOI:10.1021/acs.orglett.5b01859

An NBS-promoted allyloxyl addition–Claisen rearrangement–dehydrobromination cascade reaction has been developed. More than 20 substituted alkynylsulfonamides were reacted with allyl alcohols to generate (2Z)-2,4-dienamides in moderate to high yields. A mechanistic model has been proposed to account for the overall reaction sequence including the stereochemical outcome. Theoretical calculations suggested that a [3,3] sigmatropic rearrangement be the rate-limiting step.

1H-3,10a-Methano-2,4-dioxacyclohepta[bc]cyclopent[jk]acenaphthylene-1,7(4aH)-dione,2a,3,9,10,10b,10c-hexahydro-5,11-dimethyl-, (2aR,3R,4aR,10aS,10bS,10cR,11S)-

CAS:64761-48-4

1H-3,10a-Methano-2,4-dioxacyclohepta[bc]cyclopent[jk]acenaphthylene-1,7(4aH)-dione,2a,3,9,10,10b,10c-hexahydro-5,11-dimethyl-, (2aR,3R,4aR,10aS,10bS,10cR,11S)-