Convergent approaches to saudin intermediates

被引：16

作者：

Cravero, RM ^{[1
]}

González-Sierra, M ^{[1
]}

Labadie, GR ^{[1
]}

机构：

[1] Univ Nacl Rosario, Fac Ciencias Bioquim & Farmaceut, Dept Quim Organ, IQUIOS, RA-2002 Rosario, Santa Fe, Argentina

来源：

HELVETICA CHIMICA ACTA | 2003年 / 86卷 / 08期

关键词：

ENANTIOSELECTIVE SYNTHESIS; STEREOSELECTIVE SYNTHESIS; ABSOLUTE-CONFIGURATION; HOMOALLYLIC ALKOXIDES; CLUYTIA-RICHARDIANA; TRISPORIC ACIDS; KETAL BACKBONE; KETONES; STEREOCHEMISTRY; FRAGMENTATION;

D O I：

10.1002/hlca.200390223

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Different convergent approaches to the highly oxygenated sesquiterpene natural product saudin (1), has been investigated. Our strategy has included a Michael addition and aldol condensation reaction as key steps. During the synthetic development, we have found serious steric hindrance when an a-Me-substituted alkyl vinyl ketone was used. Such steric hindrance has been overcome by synthesizing the vinyl ketone 16 through an anionic fragmentation, which was carefully studied. Finally, the intermediate 18 has been synthesized in a onepot reaction from the vinyl ketone 16 and has been cyclized to obtain the promising tricyclic intermediate 20.

引用

页码：2741 / 2753

页数：13

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