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Über eine homolytische Wasserstoffverschiebung in einem Cyclohexanring. Über Steroide, 201. Mitteilung
Author(s) -
Heusler K.,
Kalvoda J.
Publication year - 1963
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19630460730
Subject(s) - chemistry , homolysis , stereochemistry , bond cleavage , medicinal chemistry , pregnane , methyl group , derivative (finance) , organic chemistry , group (periodic table) , radical , financial economics , economics , catalysis
The homolytic cleavage of the 5,6‐bond initiated by treatment of 3β,20β‐di‐acetoxy‐6α‐methyl‐6β‐hydroxy‐5α‐pregnane with lead tetraacetate is followed by a transannular homolytic hydrogen transfer from C‐1 to C‐5, rotation of ring A around the C‐9/C‐10 bond and recyclisation to a pregnane with an inverted 10‐methyl group. The rearranged product has been converted into 6α‐methyl‐10α‐progesterone, which was then transformed into its 1‐dehydro derivative. The course of the reaction was investigated by specific deuterium labelling.