石杉碱甲及其类似物吡啶稠合手性双环[3.3.1]壬烷骨架的不对称构建

Huaiyu Bin; Li Cheng; Xiaohui Yang; Jianhua Xie; Qilin Zhou

doi:10.6023/cjoc202105059

石杉碱甲及其类似物吡啶稠合手性双环[3.3.1]壬烷骨架的不对称构建

Translated title of the contribution: Enantioselective Construction of the Pyridine-Fused Chiral Bicyclo- [3.3.1]nonane Skeleton of Huperzine A and Its Analogues

Huaiyu Bin
, Li Cheng
, Xiaohui Yang
, Jianhua Xie^*
, Qilin Zhou

^*Corresponding author for this work

Nankai University

Research output: Contribution to journal › Article › peer-review

4 Citations (Scopus)

Abstract

A concise strategy for the enantioselective construction of the pyridine-fused chiral bicyclo[3.3.1]nonane skeleton of (+)-huperzine A and its nanlogues was reported. The key features of this strategy are the catalytic asymmetric hydrogenation of an exocyclic γ, δ-unsaturated β-ketoester via dynamic kinetic resolution combined with an intramolecular arylation as the key steps to constuct the pyridine-fused chiral bicyclo[3.3.1]nonane skeleton. This strategy provides a concise and rapid approach to the chiral core structure of huperzine A and its nanlogues from the known starting materials (5 steps and 17.4% overall yield).

Translated title of the contribution	Enantioselective Construction of the Pyridine-Fused Chiral Bicyclo- [3.3.1]nonane Skeleton of Huperzine A and Its Analogues
Original language	Chinese (Traditional)
Pages (from-to)	4021-4027
Number of pages	7
Journal	Chinese Journal of Organic Chemistry
Volume	41
Issue number	10
DOIs	https://doi.org/10.6023/cjoc202105059
Publication status	Published - Oct 2021
Externally published	Yes

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title = "石杉碱甲及其类似物吡啶稠合手性双环[3.3.1]壬烷骨架的不对称构建",

abstract = "A concise strategy for the enantioselective construction of the pyridine-fused chiral bicyclo[3.3.1]nonane skeleton of (+)-huperzine A and its nanlogues was reported. The key features of this strategy are the catalytic asymmetric hydrogenation of an exocyclic γ, δ-unsaturated β-ketoester via dynamic kinetic resolution combined with an intramolecular arylation as the key steps to constuct the pyridine-fused chiral bicyclo[3.3.1]nonane skeleton. This strategy provides a concise and rapid approach to the chiral core structure of huperzine A and its nanlogues from the known starting materials (5 steps and 17.4\% overall yield).",

keywords = "Arylation, Asymmetric hydrogenation, Bicyclo[3.3.1]nonane skeleton, Huperzine A, Unsaturated ketoester",

author = "Huaiyu Bin and Li Cheng and Xiaohui Yang and Jianhua Xie and Qilin Zhou",

note = "Publisher Copyright: {\textcopyright} 2021 Chinese Chemical Society \& SIOC, CAS.",

year = "2021",

month = oct,

doi = "10.6023/cjoc202105059",

language = "繁体中文",

volume = "41",

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journal = "Chinese Journal of Organic Chemistry",

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TY - JOUR

T1 - 石杉碱甲及其类似物吡啶稠合手性双环[3.3.1]壬烷骨架的不对称构建

AU - Bin, Huaiyu

AU - Cheng, Li

AU - Yang, Xiaohui

AU - Xie, Jianhua

AU - Zhou, Qilin

PY - 2021/10

Y1 - 2021/10

N2 - A concise strategy for the enantioselective construction of the pyridine-fused chiral bicyclo[3.3.1]nonane skeleton of (+)-huperzine A and its nanlogues was reported. The key features of this strategy are the catalytic asymmetric hydrogenation of an exocyclic γ, δ-unsaturated β-ketoester via dynamic kinetic resolution combined with an intramolecular arylation as the key steps to constuct the pyridine-fused chiral bicyclo[3.3.1]nonane skeleton. This strategy provides a concise and rapid approach to the chiral core structure of huperzine A and its nanlogues from the known starting materials (5 steps and 17.4% overall yield).

AB - A concise strategy for the enantioselective construction of the pyridine-fused chiral bicyclo[3.3.1]nonane skeleton of (+)-huperzine A and its nanlogues was reported. The key features of this strategy are the catalytic asymmetric hydrogenation of an exocyclic γ, δ-unsaturated β-ketoester via dynamic kinetic resolution combined with an intramolecular arylation as the key steps to constuct the pyridine-fused chiral bicyclo[3.3.1]nonane skeleton. This strategy provides a concise and rapid approach to the chiral core structure of huperzine A and its nanlogues from the known starting materials (5 steps and 17.4% overall yield).

KW - Arylation

KW - Asymmetric hydrogenation

KW - Bicyclo[3.3.1]nonane skeleton

KW - Huperzine A

KW - Unsaturated ketoester

UR - https://www.scopus.com/pages/publications/85116774705

U2 - 10.6023/cjoc202105059

DO - 10.6023/cjoc202105059

M3 - 文章

AN - SCOPUS:85116774705

SN - 0253-2786

VL - 41

SP - 4021

EP - 4027

JO - Chinese Journal of Organic Chemistry

JF - Chinese Journal of Organic Chemistry

IS - 10

ER -

石杉碱甲及其类似物吡啶稠合手性双环[3.3.1]壬烷骨架的不对称构建

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