Synthesis of 2-(16,17-Epoxy-3β,20-dihydroxypregn-5-en-20-yl)-1,3-dithiane from Diosgenin

Synthesis of 2-(16,17-Epoxy-3β,20-dihydroxypregn-5-en-20-yl)-1,3-dithiane from Diosgenin

–2-(16,17-Epoxy-3β,20-dihydroxypregn-5-en-20-yl)-1,3-dithiane, a new promising synthon for the OSW-1 aglycone and its analogs, was synthesized from diosgenin. In an alternative approach, a low-temperature version of the decyclization of the diosgenin F-ring by the action of the Et 3 SiOTf –(CF 3 CO)...

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Bibliographic Details
Published in:Russian journal of organic chemistry Vol. 58; no. 11; pp. 1641 - 1647
Main Authors: Valiullina, Z. R., Khasanova, L. S., Miftakhov, M. S.
Format: Journal Article
Language:English
Published: Moscow Pleiades Publishing 01-11-2022
Springer Nature B.V
Subjects:
Chemistry
Chemistry and Materials Science
Dichloromethane
Low temperature
Organic Chemistry
steroids
epoxidation
1,3-dithiane
glycosides
diosgenin
OSW-1
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Summary:–2-(16,17-Epoxy-3β,20-dihydroxypregn-5-en-20-yl)-1,3-dithiane, a new promising synthon for the OSW-1 aglycone and its analogs, was synthesized from diosgenin. In an alternative approach, a low-temperature version of the decyclization of the diosgenin F-ring by the action of the Et 3 SiOTf –(CF 3 CO) 2 O–CH 2 Cl 2 system was implemented to obtain pseudodiosgenin bis-trifluoroacetate, which was then transformed in the key block.
ISSN:1070-4280
1608-3393
DOI:10.1134/S1070428022110124