Stereoselective synthesis and determination of the cytotoxic properties of spicigerolide and three of its stereoisomers

被引：40

作者：

Falomir, E

Murga, J

Ruiz, P

Carda, M

Marco, JA ^{[1
]}

Pereda-Miranda, R

Fragoso-Serrano, M

Cerda-García-Rojas, CM

机构：

[1] Univ Jaume 1, Dept Quim Inorgan & Organ, E-12080 Castellon de La Plana, Spain

[2] Univ Valencia, Dept Quim Organ, E-46100 Burjassot, Spain

[3] Univ Nacl Autonoma Mexico, Fac Quim, Dept Farm, Mexico City 04510, DF, Mexico

[4] Inst Politecn Nacl, Ctr Invest & Estudios Avanzados, Dept Quim, Mexico City 07000, DF, Mexico

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2003年 / 68卷 / 14期

关键词：

D O I：

10.1021/jo034470y

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Stereoselective syntheses of the naturally occurring, cytotoxic lactone spicigerolide and three nonnatural stereoisomers thereof are described. The commercially available sugar L-rhamnose was in all cases the chiral starting material. Key steps in each of these syntheses were asymmetric Brown allylations and ring-closing metatheses. The cytotoxic activities of the four lactones against a range of tumoral lines were then determined.

引用

页码：5672 / 5676

页数：5

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