75212-02-1Relevant articles and documents
PALLADIUM-CATALYZED SYNTHESIS OF DIENYNES RELATED TO 1α,25-DIHYDROXYVITAMIN D3
Castedo, L.,Mascarenas, J. L.,Mourino, A.,Sarandeses, L. A.
, p. 1203 - 1206 (1988)
This note describes an efficient synthesis of a 25-functionalized dienyne precursor of the natural hormone 1α,25-dihydroxyvitamin D3 which allows easy labelling on the side chain.
Palladium-catalysed coupling of vinyl triflates with enynes and its application to the synthesis of 1α,25-dihydroxyvitamin D3
Mascarenas,Sarandeses,Castedo,Mourino
, p. 3485 - 3498 (2007/10/02)
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 side chain in the final steps of the synthesis.
STEREOSPECIFIC SYNTHESIS OF THE LYTHGOE'S RING A ALDEHYDE FOR THE PREPARATION OF 1α-HYDROXYLATED TACHYSTEROLS AND CALCIFEROLS
Baggiolini, Enrico G.,Hennessy, Bernard M.,Iacobelli, Jerome A.,Uskokovic, Milan R.
, p. 2095 - 2098 (2007/10/02)
The dihydroxyaldehyde 1, an important intermediate for the synthesis of 1α-hydroxylated vitamin D derivatives via the corresponding tachysterol precursors, was prepared from (S)-(+)-carvone (6).The sequence involves as central step, the decarboxylation an