ASYMMETRIC-SYNTHESIS OF (-)-DENTICULATIN-A AND (-)-DENTICULATIN-B VIA GROUP-SELECTIVE ALDOLIZATION OF A MESO DIALDEHYDE WITH A CHIRAL N-PROPIONYLSULTAM

被引：27

作者：

OPPOLZER, W

DEBRABANDER, J

WALTHER, E

BERNARDINELLI, G

机构：

[1] Départment de Chimie Organique, Université de Genève

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 25期

关键词：

D O I：

10.1016/0040-4039(95)00787-D

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Aldolization of meso dialdehyde 3 with a borylenolate obtained from chiral N-propionylsultam 4 yields efficiently lactols 5 with simultaneous generation of five stereogenic centers. Dithioketalization/O-desilylation of 5 affords acyclic diol 9 which is converted into the marine polypropionates 1a and 1b via the asymmetric alkylation of N-propionyltoluenesultam 11 and the aldol coupling 10 + 15 --> 16.

引用

页码：4413 / 4416

页数：4

共 25 条

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