Biomimetic Enantioselective Total Synthesis of (-)-Mycoleptodiscin A

被引：28

作者：

Dethe, Dattatraya H. ^{[1
]}

Sau, Susanta Kumar ^{[1
]}

Mahapatra, Samarpita ^{[1
]}

机构：

[1] Indian Inst Technol Kanpur, Dept Chem, Kanpur 208016, Uttar Pradesh, India

来源：

ORGANIC LETTERS | 2016年 / 18卷 / 24期

关键词：

PROTECTING GROUPS; ALKALOIDS; INDOLOSESQUITERPENE; HAPALINDOLES;

D O I：

10.1021/acs.orglett.6b03292

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Biomimetic total synthesis of (-)-mycoleptodiscin A (1) was achieved starting from the enantiopure key intermediate, which was prepared by Friedel-Crafts reaction between 7-methoxyindole and chiral primary allylic alcohol. The crucial step in this synthesis was an intramolecular Friedel-Crafts reaction at C-4 of the indole derivative driven by the EDG/EWG within a compound that was rationally designed to prevent the cyclization reaction at the C-2 positon of indole, thereby successfully providing the complete carbon framework of 1. This intramolecular Friedel-Crafts reaction at C-4 of indole derivative could be applied for the synthesis of other C-4-substituted indole alkaloid natural products.

引用

页码：6392 / 6395

页数：4

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