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Steroidal cyclobutanones, I. Synthesis and stereochemistry of steroidal spirocyclobutanones
Author(s) -
Paryzek Zdzislaw,
Blaszczyk Krzysztof
Publication year - 1990
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.1990199001126
Subject(s) - chemistry , methylene , cycloaddition , stereochemistry , double bond , medicinal chemistry , organic chemistry , catalysis
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.