Synthesis of tedanolide and 13-deoxytedanolide. Assembly of a common C(1)-C(11) subtarget

被引：56

作者：

Smith, AB ^{[1
]}

Lodise, SA

机构：

[1] Univ Penn, Dept Chem, Lab Res Struct Mat, Philadelphia, PA 19104 USA

[2] Univ Penn, Monell Chem Senses Ctr, Philadelphia, PA 19104 USA

来源：

ORGANIC LETTERS | 1999年 / 1卷 / 08期

关键词：

D O I：

10.1021/ol9909233

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] In this Letter we describe a synthetic strategy and an efficient assembly of a common C(1)-C(11) subtarget, (-)-3, for (+)-tedanolide (1) and (+)-13-deoxytedanolide (2), architecturally complex marine macrolides displaying potent antitumor activity. Key elements of the synthesis include two iterations of the Evans aldol protocol to construct the C(1)-C(6) moiety and a stereocontrolled vinyl anion addition to generate the C(8,9) trisubstituted olefin incorporating stereogenicity at C(7). Alkylation with a model epoxide demonstrates that (-)-3 is a competent dithiane for further elaboration of the macrolide skeleton.

引用

页码：1249 / 1252

页数：4

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