Some reactions of 16 alpha,17 alpha-oxido-steroids: a study related to the synthesis of the potent anti-tumor Saponin OSW-1 aglycone

Five 16 alpha,17 alpha-oxido-steroids were subjected to acids, bases and lithium hydroperoxide. Acids caused Wagner-Meerwein-type rearrangement irrespective of the side-chain structure. The 16 alpha,17 alpha-epoxides proved resistant to bases unless a C(22)=O group was present; in the case of 22-est...

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Bibliographic Details
Published inTetrahedron letters Vol. 41; no. 19; pp. 3751 - 3754
Main Authors Morzycki, JW, Gryszkiewicz, A, Jastrzebska
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 06.05.2000
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
sapogenins
ORNITHOGALUM-SAUNDERSIAE
BULBS
steroids
lithium compounds
CHOLESTANE GLYCOSIDES
epoxides
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Summary:Five 16 alpha,17 alpha-oxido-steroids were subjected to acids, bases and lithium hydroperoxide. Acids caused Wagner-Meerwein-type rearrangement irrespective of the side-chain structure. The 16 alpha,17 alpha-epoxides proved resistant to bases unless a C(22)=O group was present; in the case of 22-esters or 22-ketones the oxirane rings were cleaved with base and the corresponding allylic alcohols were formed. The reactions of 16 alpha,17 alpha-oxido-22-carbonyl compounds with lithium hydroperoxide resulted in the epoxide cleavage to the desired 16 beta,17 alpha-diols which underwent further transformations. (C) 2000 Elsevier Science Ltd. All rights reserved.
ISSN:0040-4039
DOI:10.1016/S0040-4039(00)00484-6