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Synthesis and oxidation of pregna‐3,5‐dien‐20‐ols and ‐20‐one and selective reduction of pregna‐3,5‐dien‐20‐one
Author(s) -
Göndös György,
Orr James C.
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.199019900139
Subject(s) - chemistry , reagent , pregnane , reducing agent , organic chemistry , medicinal chemistry
Pregna‐3,5‐dien‐20‐one ( 4 ) and (20S)‐ and (20R)‐pregna‐3,5‐dien‐20‐ol ( 2 and 3 ) were synthesized from progesterone. Oxidation of a mixture of 2 and 3 with Jones reagent gave 4 , while a large excess of Jones reagent afforded besides 4 , 6‐oxoprogesterone ( 5 ), 6β‐hydroxyprogesterone ( 6 ) and 5α‐pregnane‐3,6,20‐trione ( 7 ). With L‐selectride as reducing agent, reduction of 4 led to 2 and 3 in a ratio of about 1:1. However, some reducing agents gave a higher ratio of isomer 3 .