J Org Chem. 2006 Jul 7;71(14):5361-4.

Enantioselective synthesis of a key "A-ring" intermediate for the preparation of 1alpha-fluoro vitamin D3 analogues.

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University of Oxford, Chemistry Research Laboratory, 12 Mansfield Road, Oxford OX1 3TA, U.K.

Abstract

1Alpha-fluoro A-ring dienol 2, a useful building block for the preparation of fluorinated vitamin D3 analogues, was synthesized in eight steps from 4-{[tert-butyldimethylsilyl]oxy}cyclohexanone. The most distinctive synthetic development to emerge from this new synthesis is an unprecedented substrate-controlled diastereoselective fluorodesilylation of an advanced dienylsilane intermediate. This is the first enantioselective route to compound 2 relying on the use of an electrophilic fluorinating reagent.

PMID:: 16808527; [PubMed - indexed for MEDLINE]

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