Stereocontrolled Synthesis of (±)-Melokhanine E via an Intramolecular Formal [3+2] Cycloaddition

被引：9
|
作者：
Cholewczynski, Anna E.
Williams, Peyton C.
Pierce, Joshua G.
机构：
[1] Department of Chemistry, College of Sciences, NC State University, Raleigh, 27695, NC
来源：
ORGANIC LETTERS | 2020年 / 22卷 / 02期
关键词：
ALLYLIC ALKYLATION; NATURAL-PRODUCTS; METHODOLOGY;
D O I：
10.1021/acs.orglett.9b04546
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A convergent sequence to access the indole alkaloid (+/-)-melokhanine E in 12-steps (8-step longest linear sequence) and an 11% overall yield is reported. The approach utilizes two cyclopropane moieties as reactive precursors to a 1,3-dipole and imine species to enable stereoselective construction of the core scaffold through a formal [3 + 2] cycloaddition. The natural product was evaluated for its antimicrobial activity based on isolation reports; however, no activity was observed. The reported efforts serve as a synthetic platform to prepare an array of alkaloids bearing this core structural motif.
引用
收藏
页码：714 / 717
页数：4
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