An Efficient Stereoselective Synthesis of a Racemic CD-Intermediate of Vitamin D

Wendy A. Loughlint, Richard K. Haynes

Research output: Contribution to journalArticlepeer-review

8 Citations (Scopus)

Abstract

A highly efficient four-step approach to the racemic CD-intermediate 8 from the racemic hydrindenone 10 has been developed. In the key step, the hydrindenone 10 is converted stereoselectively into the (±)-bromohydrindenone 17. Oxygen transposition from C-9 to C-8 is effected by meass of conversion of 17 to the epoxide 20 and regioselective reductive ring opening of 20 with DIBALH. The resulting (±)-hydrindanol 8 was converted by the Horner-Wittig reaction with ±-methacrolein into the diene 24, hydrogenation of which provided the racemic hydrindanol 25. This is a direct precursor of racemic Grundmann's ketone 9 and bears the alkyl side chain and the correct relative configuration at C13, C14, C17, and C20 of Vitamin D.

Original languageEnglish
Pages (from-to)807-812
Number of pages6
JournalJournal of Organic Chemistry
Volume60
Issue number4
DOIs
Publication statusPublished - 01 Feb 1995

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