Advanced Synthesis and Catalysis p. 214 - 219 (1996)
Update date:2022-09-26
Topics:
Wittmann
Krieg
Prousa
Schoenecker
Droescher
Efficient three-step approaches to the two 3-epimeric 22-tosylated 1,5-diene-3,22-diols 6 and 7 starting with (20S)-20-(hydroxymethyl)pregna-1,4-dien-3-one (1) were developed and optimized. Isomerization of 1 to the 1,5-dien-3-one 3 and subsequent tosylation furnished the deconjugated 3-ketone 4. The 3β-alcohol 6 was available from 4 by means of in situ generated calcium borohydride. Treatment of 4 with lithium trisiamylborohydride (LS-Selectride) afforded the highest yield of the hitherto unknown 3α-epimer 7. Following the optimized synthesis, 6 and 7 were obtained from 1 in 60 % and 50 % overall yield, respectively.
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