Synthesis of spiro[4.5]decane CF-ring analogues of 1 alpha,25-dihydroxyvitamin D3.
A novel series of analogues of calcitriol (1) is developed featuring a spirocyclic central core resulting from C18/C21-connection and C15/C16-deletion (2a, 2b). The synthesis of the key intermediate involves an Eschenmoser rearrangement of an enantiomerically pure bromo-substituted cyclohexenol.
Schepens
Wim
W
Department of Organic Chemistry, Ghent University, Krijgslaan 281, B-9000 Gent, Belgium.
Van Haver
Dirk
D
Vandewalle
Maurits
M
Bouillon
Roger
R
Verstuyf
Annemieke
A
De Clercq
Pierre J
PJ
D000473:Alkanes / Q000737:chemistry*; D002117:Calcitriol / Q000138:chemical synthesis* / Q000737:chemistry; D002851:Chromatography, High Pressure Liquid; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013237:Stereoisomerism
D000473:Alkanes; D002117:Calcitriol; C012867:decane