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Steroidal cyclobutanones, I. Synthesis and stereochemistry of steroidal spirocyclobutanones

✍ Scribed by Paryzek, Zdzislaw ;Blaszczyk, Krzysztof

Book ID
102901318
Publisher
John Wiley and Sons
Year
1990
Tongue
English
Weight
669 KB
Volume
1990
Category
Article
ISSN
0947-3440

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✦ Synopsis

Abstract

Cycloaddition of dichloroketene to 3‐, 7‐, and 17‐methylene steroids affords the corresponding spirodichlorocyclobutanones, which can be reduced to monochloro‐ and unsubstituted spirocyclobutanones. Selective cycloaddition to the exo‐double bond is observed in the reaction of 3β‐acetoxy‐17‐methylene‐5‐androstene. The stereochemistry of spiro compounds is assigned on the basis of ^1^H‐ and ^13^C‐NMR spectra. Some steroidal spirolactones are obtained and their stereochemistry is assigned.

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