Total Synthesis of Calophyline A

被引：51

作者：

Li, Guang ^{[1
]}

Xie, Xiaoni ^{[1
]}

Zu, Liansuo ^{[1
,2
,3
]}

机构：

[1] Tsinghua Univ, Sch Pharmaceut Sci, Beijing 100084, Peoples R China

[2] Sichuan Univ, Collaborat Innovat Ctr Biotherapy, State Key Lab Biotherapy, Chengdu 610041, Peoples R China

[3] Sichuan Univ, West China Hosp, West China Med Sch, Ctr Canc, Chengdu 610041, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2016年 / 55卷 / 35期

关键词：

aldol reactions; alkaloids; natural products; rearrangements; total synthesis; ENANTIOSELECTIVE TOTAL-SYNTHESIS; STEREOCONTROLLED SYNTHESIS; AKUAMMILINE ALKALOIDS; GENERAL STRATEGY; UNIFIED STRATEGY; NATURAL-PRODUCTS; HECK REACTION; STRYCHNOS; ACCESS; WELL;

D O I：

10.1002/anie.201604770

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Reported herein is the total synthesis of calophyline A, an indoline natural product possessing distinct ring connectivity which has not been synthesized previously. The synthetic route features several key transformations, including an aza-pinacol rearrangement to construct the nitrogen-containing bridged [3.2.2] bicycle, a Heck cyclization to assemble the fused 6/5/6/5 ring system, and a challenging late-stage aldol reaction to generate both a neopentyl quaternary stereogenic center and an oxygen-containing bridged [3.2.1] bicycle.

引用

页码：10483 / 10486

页数：4

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