Step-Economical Synthesis of the Marine Ascidian Antibiotics Cadiolide A, B, and D

被引：28

作者：

Boukouvalas, John ^{[1
]}

Thibault, Charles ^{[1
]}

机构：

[1] Univ Laval, Dept Chim, Quebec City, PQ G1V 0A6, Canada

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2015年 / 80卷 / 01期

基金：

加拿大自然科学与工程研究理事会;

关键词：

EFFICIENT SYNTHESIS; VANCOMYCIN RESISTANCE; SELECTIVE SYNTHESIS; RUBROLIDES C; SYNOICUM; FACILE; KNOEVENAGEL; ACID; METABOLITES; INHIBITION;

D O I：

10.1021/jo502503w

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A concise, modular and efficient synthesis of the title natural products is reported. Prominent steps include (i) one-pot assembly of a key beta-aryl-alpha-benzoylbutenolide building block by regiocontrolled click-unclick oxazole-ynone Diels-Alder cycloaddition/cycloreversion and ensuing 2-alkoxyfuran hydrolysis and (ii) a protecting group-free vinylogous Knoevenagel condensation enabling rapid access to cadiolides A, B, and D from a common precursor.

引用

页码：681 / 684

页数：4

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