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Synthesis of Spiro[4.5]decane CF-Ring Analogues of 1α,25-Dihydroxyvitamin D3

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journal contribution
posted on 14.09.2006, 00:00 authored by Wim Schepens, Dirk Van Haver, Maurits Vandewalle, Roger Bouillon, Annemieke Verstuyf, Pierre J. De Clercq
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.