Tetrahedron

Palladium-catalysed coupling of vinyl triflates with enynes and its application to the synthesis of 1α, 25-dihydroxyvitamin D 3

JL Mascareñas, LA Sarandeses, L Castedo, A Mouriño

Index: Mascarenas; Sarandeses; Castedo; Mourino Tetrahedron, 1991 ,  vol. 47,  # 20-21  p. 3485 - 3498

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Citation Number: 76

Abstract

We describe a general approach, based on the palladium-catalysed coupling of enynes with vinyl triflates, for the construction of dienynes related to vitamin D metabolites and analogues. As an application of this method, an efficient convergent synthesis of 1α, 25- dihydroxyvitamin D3 starting from the Inhoffen-Lythgoe diol (6a) and natural carvones has been carried out (11 steps, 28% overall yield from 6a). This strategy allows labelling of the ...