SYNTHESIS OF ALKENE DIPEPTIDE ISOSTERES EMPLOYING THE WITTIG-STILL REARRANGEMENT

被引：30

作者：

BOL, KM ^{[1
]}

LISKAMP, RMJ ^{[1
]}

机构：

[1] LEIDEN UNIV,GORLAEUS LABS,POB 9502,2300 RA LEIDEN,NETHERLANDS

来源：

TETRAHEDRON | 1992年 / 48卷 / 31期

关键词：

D O I：

10.1016/S0040-4020(01)88232-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new approach to the synthesis of alkene dipeptide isosteres is reported which features the use of the [2,3]-Wittig-Still rearrangement, carried out in hexanes. Employing this rearrangement alkene dipeptide isosteres of ''Gly-Xxx'' are accessible starting from an alpha-beta-unsaturated carbonyl compound. This is illustrated with the synthesis of the alkene dipeptide isostere of Gly-Ala as part of the tripeptide isostere Cbz-Phe-Gly-psi[E-CH=CH]-(R,S)Ala-OH 20, starting from crotonaldehyde. Alkene dipeptide isosteres of''Xxx-Gly'' arc accessible starting from an a-amino aldehyde derivative. As an example the synthesis of the dipeptide isostere of Phe-Gly as part of the tripeptide isostere Cbz-Phe-Phe-psi[E-CH=CH]-Gly-OH 28 is described for which N-Tr-phenylalaninal was used as a starting material.

引用

页码：6425 / 6438

页数：14

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