Pentacyclic Furanosteroids: The Synthesis of Potential Kinase Inhibitors Related to Viridin and Wortmannolone

被引：21

作者：

Lang, Yunhui ^{[1
]}

Souza, Fabio E. S. ^{[1
]}

Xu, Xinshe ^{[1
]}

Taylor, Nicholas J. ^{[1
]}

Assoud, Abdeljalil ^{[1
]}

Rodrigo, Russell ^{[1
]}

机构：

[1] Univ Waterloo, Dept Chem, Waterloo, ON N2L 3G1, Canada

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 74卷 / 15期

基金：

加拿大自然科学与工程研究理事会;

关键词：

DIELS-ALDER REACTIONS; PHOSPHOINOSITIDE; 3-KINASE; RING-SYSTEM; CYCLOADDITIONS; ALKALOIDS; CHEMISTRY;

D O I：

10.1021/jo900922q

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A regiocontrolled intermolecular Diels-Alder reaction of all o-benzoquinone followed by all intramolecular nitrile oxide cyclization is employed to prepare the BCD fragment of viridin. The AE segment is attached to it by means of an intramolecular Diels-Alder reaction of an o-benzoquinone monoketal generated in situ from tricycle 15 and 5-trimethylsilyl-2E,4E-pentadienol 20. The silyl substituent at C-1 of the pentacyclic product directs the dihydroxylation of the C-2-C-3 double bond to its beta-face. Various transformations of the 1-trimethylsilyi-2 beta,3 beta-dihydroxy pentacycle into several others with oxygen substituents in ring A are described. One of these products 40 possesses the same structure and relative stereochemistry in rings A, B, and E as that of the natural product wortmannolone 3.

引用

页码：5429 / 5439

页数：11

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