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

✍ Scribed by Jacek W Morzycki; Agnieszka Gryszkiewicz; Izabella Jastrzębska

Publisher: Elsevier Science
Year: 2000
Tongue: French
Weight: 203 KB
Volume: 41
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)00484-6

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✦ Synopsis

Five 16α,17α-oxido-steroids were subjected to acids, bases and lithium hydroperoxide. Acids caused Wagner-Meerwein-type rearrangement irrespective of the side-chain structure. The 16α,17α-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 16α,17α-oxido-22carbonyl compounds with lithium hydroperoxide resulted in the epoxide cleavage to the desired 16β,17α-diols which underwent further transformations.

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