Synthesis of the C(1)-C(12) segment of peloruside A by an α-benzyloxymethyl ketone aldol strategy

被引：28

作者：

Engers, DW ^{[1
]}

Bassindale, MJ ^{[1
]}

Pagenkopf, BL ^{[1
]}

机构：

[1] Univ Texas, Dept Chem & Biochem, Austin, TX 78712 USA

来源：

ORGANIC LETTERS | 2004年 / 6卷 / 05期

关键词：

D O I：

10.1021/ol036393z

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The C(1)-C(12) segment of 16-membered antitumor macrolide peloruside A has been prepared by a (BF3OEt2)-O-.-catalyzed Mukaiyama aldol reaction between a glucose-derived C(1)-C(7) aldehyde and a C(8)-C(12) alpha-benzyloxymelhyl ketone. Exclusive 2,3-anti and moderate 3,5-anti/syn facial selectivity (3.5:1) was observed in the aldol reaction. The key C(1)-C(7) aldehyde contains the required stereochemistry at carbons two, three, and five, and has been efficiently prepared on multigram scales from commercial triacetyl D-glucal.

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页码：663 / 666

页数：4

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