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
收藏
页码：3500 / 3503
页数：4
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