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

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

A synthesis of enantiopure 19-nor-Vitamin D(3) 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...

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Veröffentlicht in:Chemical communications (Cambridge, England) England), 2012-09, Vol.48 (72), p.9077-9079
Hauptverfasser: Sikervar, Vikas, Fleet, James C, Fuchs, Philip L
Format: Artikel
Sprache:eng
Schlagworte:
Chemistry Techniques, Synthetic
Cholecalciferol - analogs & derivatives
Cholecalciferol - chemical synthesis
Cyclohexanes - chemical synthesis
Models, Molecular
Molecular Conformation
Phosphates - chemistry
Stereoisomerism
Sulfones - chemical synthesis
Sulfones - chemistry
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Zusammenfassung:A synthesis of enantiopure 19-nor-Vitamin D(3) 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 LiBH(4) mediated sequential bis reduction of an epoxy vinyl sulfone.
ISSN:1359-7345
1364-548X
DOI:10.1039/c2cc33054g