Total Synthesis of (±)-Strictamine

被引：69

作者：

Ren, Weiwu ^{[1
]}

Wang, Qian ^{[1
]}

Zhu, Jieping ^{[1
]}

机构：

[1] Ecole Polytech Fed Lausanne, Inst Chem Sci & Engn, Lab Synth & Nat Prod, SB,ISIC,LSPN,BCH 5304, CH-1015 Lausanne, Switzerland

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2016年 / 55卷 / 10期

基金：

瑞士国家科学基金会;

关键词：

alkaloids; cyclization; heterocycles; natural products; total synthesis; ENANTIOSELECTIVE TOTAL-SYNTHESIS; ENANTIOSPECIFIC TOTAL-SYNTHESIS; CONCISE TOTAL-SYNTHESIS; INDOLE ALKALOIDS; STRYCHNOS ALKALOIDS; GENERAL-APPROACH; STEREOCONTROLLED SYNTHESIS; AKUAMMILINE ALKALOIDS; CYCLIZATION; DEMETHYLATION;

D O I：

10.1002/anie.201511638

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The total synthesis of strictamine has been achieved in nine steps from a known enol triflate. Characteristic features of our approach included: a)creation of a C7 all-carbon quaternary stereocenter at an early synthetic stage; b)use of an N,N-dimethyl tertiary amine as a surrogate of the primary amine for the rapid build-up of a functionalized 2-azabicyclo[3,3,1]nonan-9-one skeleton (achieved by using a reaction sequence of -bromination of the ketone, followed by a stereoconvergent intramolecular nucleophilic substitution reaction); and c)a late-stage construction of the indolenine unit.

引用

页码：3500 / 3503

页数：4

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