Asymmetric Total Synthesis of (-)-Spirochensilide A

被引：44

作者：

Liang, Xin-Ting ^{[1
,2
,3
]}

Chen, Jia-Hua ^{[1
,2
,3
]}

Yang, Zhen ^{[1
,2
,3
,4
,5
]}

机构：

[1] Peking Univ, Key Lab Bioorgan Chem & Mol Engn, Minist Educ, Beijing 100871, Peoples R China

[2] Peking Univ, Beijing Natl Lab Mol Sci, Beijing 100871, Peoples R China

[3] Peking Univ, Peking Tsinghua Ctr Life Sci, Beijing 100871, Peoples R China

[4] Peking Univ, State Key Lab Chem Oncogen, Shenzhen Grad Sch, Shenzhen 518055, Peoples R China

[5] Shenzhen Wan Lab, Shenzhen 518055, Peoples R China

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2020年 / 142卷 / 18期

基金：

美国国家科学基金会;

关键词：

PAUSON-KHAND REACTION; CROSS-ALDOL REACTION; ENANTIOSELECTIVE SYNTHESIS; SINGLET OXYGEN; CYCLIZATION; CONSTRUCTION; REARRANGEMENT; TRITERPENOIDS; COMPLEXES; PRODUCTS;

D O I：

10.1021/jacs.0c02522

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An asymmetric total synthesis of (-)-spirochensilide A has been achieved for the first time. The synthesis features a semipinacol rearrangement reaction to stereoselectively construct the two-vicinal quaternary chiral centers at C8 and C10, a tungsten-mediated cyclopropene-based Pauson-Khand reaction to install the C13 quaternary chiral center, and a furan-based oxidative cyclization to stereoselectively form the spiroketal motif.

引用

页码：8116 / 8121

页数：6

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