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

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.
Publication status:
Published

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Publisher copy:
10.1021/jo060516m

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Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Role:
Author
Journal:
The Journal of organic chemistry
Volume:
71
Issue:
14
Pages:
5361-5364
Publication date:
2006-07-05
DOI:
EISSN:
1520-6904
ISSN:
0022-3263
URN:
uuid:4f0658d1-f7e8-4543-8f4c-ac98a0d3a844
Source identifiers:
33523
Local pid:
pubs:33523

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