Unified Total Syntheses of (±)-Sessilifoliamides B, C, and D

被引：11
|
作者：
Olivier, Wesley J. [1 ]
Bissember, Alex C. [1 ]
Smith, Jason A. [1 ]
机构：
[1] Univ Tasmania, Sch Nat Sci Chem, Hobart, Tas 7001, Australia
来源：
ORGANIC LETTERS | 2021年 / 23卷 / 09期
关键词：
ALKALOIDS; PYRROLES; OXIDATION;
D O I：
10.1021/acs.orglett.1c00895
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The first total syntheses of the Stemona alkaloids sessilifoliamides B and D and the second synthesis of sessilifoliamide C have been completed from a simple pyrrole substrate. The bicyclic lactam core was prepared on a gram scale via a Bronsted acid mediated cyclization and controlled oxidation with Dess-Martin periodinane. This delivered sessilifoliamide C (and its C-11 epimer) in 24% yield over 11 steps, and sessilifoliamides B and D in 13 and 17 steps, respectively.
引用
收藏
页码：3437 / 3441
页数：5
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