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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