General Synthesis of the Nitropyrrolin Family of Natural Products via Regioselective CO2-Mediated Alkyne Hydration

被引：20

作者：

Ding, Xiao-Bo

Furkert, Daniel P. ^{[1
]}

Brimble, Margaret A. ^{[1
]}

机构：

[1] Univ Auckland, Sch Chem Sci, 23 Symonds St, Auckland 1142, New Zealand

来源：

ORGANIC LETTERS | 2017年 / 19卷 / 19期

关键词：

PROPARGYLIC ALCOHOLS; CARBON-DIOXIDE; ASYMMETRIC-SYNTHESIS; AMBIENT CONDITIONS; HERONAPYRROLE C; DEPROTONATION; BIOSYNTHESIS; CYCLIZATION; REDUCTION; ACIDS;

D O I：

10.1021/acs.orglett.7b02687

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The total synthesis of the 2-nitropyrrole natural products nitropyrrolins A and B and the formal synthesis of nitropyrrolin D are reported. The key 2-nitro-4-alkylpyrrole core was efficiently assembled by Sonogashira cross-coupling, with complete control of regioselectivity. An unusual carboxylative cyclization, sulfonylcarbamate formation, and base-promoted cleavage sequence enabled access to the key hydroxy ketone without affecting the protected 2-nitropyrrole unit. The total synthesis provides a general approach for preparation of the bioactive nitropyrrolin family of natural products.

引用

收藏

页码：5418 / 5421

页数：4

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