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A new strategy for the preparation of 11-oxygenated steroids synthesis of (±)-adrenosterone

✍ Scribed by Paul A. Grieco; Scott A. May; Michael D. Kaufman

Publisher
Elsevier Science
Year
1998
Tongue
French
Weight
218 KB
Volume
39
Category
Article
ISSN
0040-4039

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✦ Synopsis

Conjugate 1,4-addition of 1- [(tert-butyldimethylsilyl)oxy]-2-methyl-1,3-cyclohexadiene (5) to 2-methylcyclopentenone in highly polar media and subsequent alkylation of the resultant silyl enol ether (4) with phenylthiodienyl carbonate I0 in 5.0 M LiC104.Et20 provides substrate 2. Exposure of 2 to TMSOTf/ TMSOCH2CH2OTMS affords tetracyclic bis-ketal 3, which is convened into (+)-adrenosterone (1) in four steps.

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