873567-11-4Relevant articles and documents
Pd-catalyzed carbocyclization-negishi cross-coupling cascade: A novel approach to 1α,25-dihydroxyvitamin D3 and analogues
Gomez-Reino, Clara,Vitale, Cristian,Maestro, Miguel,Mourino, Antonio
, p. 5885 - 5887 (2005)
(Chemical Equation Presented) A mild palladium-catalyzed cascade has been used for the synthesis of the hormone 1α,25-dihydroxyvitamin D3 (calcitriol, 1a) and its analogues 1b and 1c. This one-pot process involves two consecutive transformations at room temperature: An initial palladium-catalyzed 6-exo-cyclocarbopalladation of vinyl triflates followed by a Negishi cross-coupling reaction with an alkenyl zinc. This novel strategy opens new possibilities for the preparation of a variety of new vitamin D analogues of therapeutic potential, particularly with modifications at the triene and/or ring-A.