A practical and efficient synthesis of the C-16-C-28 spiroketal fragment (CD) of the spongistatins

被引：47

作者：

Gaunt, MJ ^{[1
]}

Hook, DF ^{[1
]}

Tanner, HR ^{[1
]}

Ley, SV ^{[1
]}

机构：

[1] Univ Cambridge, Dept Chem, Cambridge CB2 1EW, England

来源：

ORGANIC LETTERS | 2003年 / 5卷 / 25期

关键词：

D O I：

10.1021/ol035848h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] A practical and efficient route to the CD spiroketal (C-16-C-28) of the spongistatins is reported. Two stereocenters are introduced from chiral building blocks with the remainder introduced by substrate-controlled transformations. The key beta-keto-1,3-dithiane intermediate is generated by a dithiol conjugate addition to an ynone and the 1,3-dithiane unit in the C-ring plays a key role in the spiroketalization and subsequent epimerization. The synthesis requires 24 steps, with a longest linear sequence of 19 steps in an overall yield of 14.5% (for the longest linear sequence).

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页码：4815 / 4818

页数：4

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