PALLADIUM-CATALYZED COUPLING OF VINYL TRIFLATES WITH ENYNES AND ITS APPLICATION TO THE SYNTHESIS OF 1-ALPHA,25-DIHYDROXYVITAMIN-D3

被引：88
|
作者：
MASCARENAS, JL [1 ]
SARANDESES, LA [1 ]
CASTEDO, L [1 ]
MOURINO, A [1 ]
机构：
[1] CSIC, SECC ALCALOIDES, E-15706 SANTIAGO, SPAIN
来源：
TETRAHEDRON | 1991年 / 47卷 / 20-21期
关键词：
D O I：
10.1016/S0040-4020(01)86410-3
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
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 1-alpha,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.
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页码：3485 / 3498
页数：14
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