'Naked sugars of the second generation': Asymmetric synthesis of long-chain polypropionates and analogues starting with acetone

被引：21

作者：

Vogel, P

Sevin, AF

Kernen, P

Bialecki, M

机构：

[1] Section de Chimie, Univ. de Lausanne BCH-Dorigny

来源：

PURE AND APPLIED CHEMISTRY | 1996年 / 68卷 / 03期

关键词：

D O I：

10.1351/pac199668030719

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Homochiral Diels-Alder adduct of 2,4-dimethylfuran to 1-cyanovinyl (1'R)- or (1'S)-camphanate are transformed readily into polypropionate fragments containing four or five contiguous stereogenic centres. They can be condensed via cross-aldolizations to lithium enolates of 7-oxabicyclo[2.2.1]heptan-2-ones with high diastereoselectivity generating long-chain systems containing up to eleven stereogenic centres and tertiary alcoholic moieties.

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页码：719 / 722

页数：4

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