Total Synthesis of the Antitumor Antibiotic Basidalin

被引：20

作者：

Acosta, Jaime A. M. ^{[1
]}

Muddala, Ramesh ^{[1
]}

Barbosa, Luiz C. A. ^{[2
]}

Boukouvalas, John ^{[1
]}

机构：

[1] Univ Laval, Dept Chem, Pavillon Alexandre Vachon,1045 Ave Med, Quebec City, PQ G1V 0A6, Canada

[2] Univ Fed Minas Gerais, Dept Chem, Inst Ciencias Exatas, Av Pres Antonio Carlos 6627, BR-31270901 Belo Horizonte, MG, Brazil

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 81卷 / 15期

基金：

加拿大自然科学与工程研究理事会;

关键词：

STEREOSELECTIVE-SYNTHESIS; ASYMMETRIC-SYNTHESIS; VINYLOGOUS ALDOL; 4-AMINO-2(5H)-FURANONES; TETRONAMIDES; INHIBITOR; AMINES; ROUTE; ACIDS;

D O I：

10.1021/acs.joc.6b01255

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first synthesis of the tetronamide antibiotic basidalin was accomplished in five steps and 39% overall yield from readily available 4-bromo-2-triisopropylsilyloxyfuran and 2-formyl-1,3-dithiane. Highlights include: (i) regio- and stereocontrolled assemblage of a pivotal (Z)-gamma-ylidene-beta-bromo-butenolide intermediate by stereodirected vinylogous aldol condensation (SVAC), (ii) installation of the amino group via aza-Michael addition/elimination, and crucially (iii) facile access to basidalin by late-stage dithiane removal.

引用

页码：6883 / 6886

页数：4

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