Yu-Rong Yang

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Name: 杨玉荣

Organization: Chinese Academy of Sciences , China

Department: Kunming Institute of Botany

Title: NULL(PhD)

TOPICS

Analytical Chemistry

Chemicals
References

Ir-Catalyzed Asymmetric Total Synthesis of (−)-Communesin F

Co-reporter:Xiao Liang, Tian-Yuan Zhang, Xue-Yi Zeng, Yu Zheng, Kun Wei, and Yu-Rong Yang

Journal of the American Chemical Society March 8, 2017 Volume 139(Issue 9) pp:3364-3364

Publication Date(Web):February 20, 2017

DOI:10.1021/jacs.7b00854

The first catalytic asymmetric total synthesis of the heptacyclic alkaloid (−)-communesin F is described. A key step features an iridium-catalyzed asymmetric intermolecular cascade cyclization, constructing the lower N,N-aminal-containing CDEF tetracyclic core in one step. Another notable element is the closure of final ring system (A ring) via a facile reduction of a twisted amide and concomitant cyclization activated by mesylation of N,O-hemiaminal intermediate.

Enantioselective Total Synthesis of (−)-Alstoscholarisine A

Co-reporter:Xiao Liang; Shi-Zhi Jiang; Kun Wei

Journal of the American Chemical Society 2016 Volume 138(Issue 8) pp:2560-2562

Publication Date(Web):February 16, 2016

DOI:10.1021/jacs.6b00625

We report a concise and highly enantioselective total synthesis of (−)-alstoscholarisine A (1), a recently isolated monoterpenoid indole alkaloid that has significant bioactivity in promoting adult neuronal stem cells proliferation. A highly enantioselective (99% ee), intramolecular Ir-catalyzed Friedel–Crafts alkylation of indole 9 with a secondary allylic alcohol was utilized to establish the first stereogenic center upon which the other three contiguous chiral centers were readily set by a highly stereoselective tandem 1,4-addition and aldol reaction. The key tetrahydropyran was constructed through a hemiacetal reduction, and the final aminal bridge was forged by a one-pot reductive amination/cyclization. The conciseness of this approach was highlighted by building core bonds in each step with a minimalist protecting group strategy.

Iridium-Catalyzed Enantioselective Indole Cyclization: Application to the Total Synthesis and Absolute Stereochemical Assignment of ()-AspidophyllineA

Co-reporter:Dr. Shi-Zhi Jiang;Xue-Yi Zeng;Xiao Liang;Ting Lei;Dr. Kun Wei; Yu-Rong Yang

Angewandte Chemie 2016 Volume 128( Issue 12) pp:4112-4116

Publication Date(Web):

DOI:10.1002/ange.201511549

Abstract

The first enantioselective total synthesis of (−)-aspidophylline A, including assignment of its absolute configuration has been accomplished. A key element of the synthesis is a highly enantioselective indole allylic alkylation/iminium cyclization cascade which was developed by employing a combination of Lewis acid activation and an iridium/ligand catalyst. This strategy relies on the direct use of 2,3-disubstituted indoles with secondary allylic alcohols appended at C2 and heteronucleophiles appended at C3, indoles which are easily prepared from simple starting materials under C−H activation conditions.

Iridium-Catalyzed Enantioselective Indole Cyclization: Application to the Total Synthesis and Absolute Stereochemical Assignment of ()-AspidophyllineA

Co-reporter:Dr. Shi-Zhi Jiang;Xue-Yi Zeng;Xiao Liang;Ting Lei;Dr. Kun Wei; Yu-Rong Yang

Angewandte Chemie International Edition 2016 Volume 55( Issue 12) pp:4044-4048

Publication Date(Web):

DOI:10.1002/anie.201511549

Abstract

Iridium-catalyzed enantioselective allylation of silyl enol ethers derived from ketones and α,β-unsaturated ketones

Co-reporter:Xiao Liang, Kun Wei and Yu-Rong Yang

Chemical Communications 2015 vol. 51(Issue 98) pp:17471-17474

Publication Date(Web):09 Oct 2015

DOI:10.1039/C5CC07221B

The unified Ir-catalyzed enantioselective allylic substitution reactions of silyl enol ethers derived from ketones and α,β-unsaturated ketones with branched, racemic allylic alcohols are described. This transformation is catalyzed by the Carreira system and proceeds without fluoride, and with high ee and b:l ratio. The synthetic utility of this method was illustrated by the concise enantioselective total synthesis of marine natural products calyxolane A, B and by the assignment of the absolute configuration of calyxolane A.

Iridium-catalyzed enantioselective synthesis of (−)- and (+)-aurantioclavine

Co-reporter:Ting Lei, Hongbin Zhang, Yu-Rong Yang

Tetrahedron Letters 2015 Volume 56(Issue 43) pp:5933-5936

Publication Date(Web):21 October 2015

DOI:10.1016/j.tetlet.2015.09.039

Collective Total Synthesis of Tetracyclic Diquinane Lycopodium Alkaloids (+)-Paniculatine, (−)-Magellanine, (+)-Magellaninone and Analogues Thereof

Co-reporter:Shi-Zhi Jiang, Ting Lei, Kun Wei, and Yu-Rong Yang

Organic Letters 2014 Volume 16(Issue 21) pp:5612-5615

Publication Date(Web):October 9, 2014

DOI:10.1021/ol502679v

The collective total synthesis of tetracyclic diquinane Lycopodium alkaloids, (+)-paniculatine, (−)-magellanine, (+)-magellaninone, and two analogues (−)-13-epi-paniculatine and (+)-3-hydroxyl-13-dehydro-paniculatine, has been accomplished. By logic-guided addition of a strategically useful hydroxyl group at C-3 of paniculatine, the formidable tetracyclic core was rapidly synthesized utilizing a site-specific and stereoselective aldol cyclization, thus making the ABD → ABCD tetracyclic approach to diquinane Lycopodium alkaloids attainable for the first time.

Isolation and Complete Structural Assignment of Lycopodium Alkaloid Cernupalhine A: Theoretical Prediction and Total Synthesis Validation

Co-reporter:Liao-Bin Dong, Ya-Nan Wu, Shi-Zhi Jiang, Xing-De Wu, Juan He, Yu-Rong Yang, and Qin-Shi Zhao

Organic Letters 2014 Volume 16(Issue 10) pp:2700-2703

Publication Date(Web):April 29, 2014

DOI:10.1021/ol500978k

Cernupalhine A (1) is a trace Lycopodium alkaloid (0.7 mg) possessing a new C17N skeleton with an unusual hydroxydihydrofuranone motif newly isolated from Palhinhaea cernua L. Its complete structural assignment, including absolute stereochemistry, was established through a combination of high-field NMR techniques and computational methods and further unequivocal confirmation by the first asymmetric total synthesis. Following the first total synthesis of lobscurinine (3), 1 was achieved via regio- and stereoselective cyanide ion addition and subsequent acid treatment.

Asymmetric total synthesis of Lycopodium alkaloid (+)-lycopladine A

Co-reporter:Tao Xu, Xiu-Li Luo, Yu-Rong Yang

Tetrahedron Letters 2013 Volume 54(Issue 22) pp:2858-2860

Publication Date(Web):29 May 2013

DOI:10.1016/j.tetlet.2013.03.097

Asymmetric total synthesis of (+)-lycopladine A (1) has been achieved. Key elements of the synthesis include an efficient Helquist annulation to assemble the cis-fused 6/5 bicycle, Stille coupling reaction to elongate the allylic side chain, and Kröhnke pyridine synthesis to set the pyridine core at the final stage.Asymmetric total synthesis of (+)-lycopladine A (1) has been achieved. Key elements of the synthesis include an efficient Helquist annulation to assemble the cis-fused 6/5 bicycle, Stille coupling reaction to elongate the allylic side chain, and Kröhnke pyridine synthesis to set the pyridine core at the final stage.

One-step synthesis of Lycopodium alkaloid (-)-huperzine W via Suzuki-Miyaura coupling

Co-reporter:Tao Xu;Shi-Zhi Jiang;Huai-Rong Luo

Natural Products and Bioprospecting 2012 Volume 2( Issue 6) pp:255-257

Publication Date(Web):2012 December

DOI:10.1007/s13659-012-0084-2

Application of the Helquist Annulation in Lycopodium Alkaloid Synthesis: Unified Total Syntheses of (−)-8-Deoxyserratinine, (+)-Fawcettimine, and (+)-Lycoflexine

Co-reporter:Yu-Rong Yang, Liang Shen, Jiu-Zhong Huang, Tao Xu, and Kun Wei

The Journal of Organic Chemistry 2011 Volume 76(Issue 10) pp:3684-3690

Publication Date(Web):April 7, 2011

DOI:10.1021/jo1023188

A unified strategy for total synthesis of the Lycopodium alkaloids (−)-8-deoxyserratinine (7), (+)-fawcettimine (1), and (+)-lycoflexine (4) is detailed. The key features include a highly efficient Helquist annulation to assemble the cis-fused 6/5 bicycle, facile construction of the aza nine-membered ring system employing double N-alkylation strategy, providing access to the common tricyclic skeleton, asymmetric Shi epoxidation, delivering the desired β-epoxide stereospecifically to furnish (−)-8-deoxyserratinine (7), SmI2 reduction of dihydroxylation derivative 35 to enable formation of (+)-fawcettimine (1), and a rapid biomimetic transformation of (+)-fawcettimine (1) into (+)-lycoflexine (4) via an intramolecular Mannich cyclization.

Total Synthesis of (−)-8-Deoxyserratinine via an Efficient Helquist Annulation and Double N-Alkylation Reaction

Co-reporter:Yu-Rong Yang, Zeng-Wei Lai, Liang Shen, Jiu-Zhong Huang, Xing-De Wu, Jun-Lin Yin and Kun Wei

Organic Letters 2010 Volume 12(Issue 15) pp:3430-3433

Publication Date(Web):June 29, 2010

DOI:10.1021/ol1012444

The first enantioselective total synthesis of (−)-8-deoxyserratinine has been achieved in 15 steps from enone 4 with 7% overall yield. The key features include a highly efficient Helquist annulation to furnish the cis-fused 6/5 bicycle, facile construction of the aza nine-membered ring system employing double N-alkylation strategy, as well as asymmetric Shi epoxidation, delivering the desired β-epoxide stereospecifically.