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Issue 72, 2012
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A general approach to the synthesis of enantiopure 19-nor-Vitamin D3 and its C-2 phosphate analogs prepared from cyclohexadienyl sulfone

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Abstract

A synthesis of enantiopure 19-nor-Vitamin D3 and its C-2 substituted cyclic phosphate analogs is achieved via in situ trapping of an α-sulfonyl anion with a CD-ring allyl chloride and 1,2-eliminative desulfonylation exploiting the basic properties of TBAF. The A-ring is prepared via anti-selective dithiane addition to vinyl sulfone and LiBH4 mediated sequential bis reduction of an epoxy vinyl sulfone.

Graphical abstract: A general approach to the synthesis of enantiopure 19-nor-Vitamin D3 and its C-2 phosphate analogs prepared from cyclohexadienyl sulfone

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Publication details

The article was received on 27 Apr 2012, accepted on 28 May 2012 and first published on 01 Aug 2012


Article type: Communication
DOI: 10.1039/C2CC33054G
Chem. Commun., 2012,48, 9077-9079

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    A general approach to the synthesis of enantiopure 19-nor-Vitamin D3 and its C-2 phosphate analogs prepared from cyclohexadienyl sulfone

    V. Sikervar, J. C. Fleet and P. L. Fuchs, Chem. Commun., 2012, 48, 9077
    DOI: 10.1039/C2CC33054G

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