Stereoselective Construction of Steroidal Side Chain from 16-Dehydropregnenolone Acetate

被引：7
作者：
Aher, Nilkanth G. [1 ]
Gonnade, Rajesh G. [2 ]
Pore, Vandana S. [1 ]
机构：
[1] Natl Chem Lab, Div Organ Chem, Pune 411008, Maharashtra, India
[2] Natl Chem Lab, Ctr Mat Characterizat, Pune 411008, Maharashtra, India
来源：
SYNLETT | 2009年 / 12期
关键词：
stereoselectivity; 16-dehydropregnenolone acetate; Heck coupling; transfer hydrogenation; steroidal side chain; PALLADIUM-CATALYZED HYDROGENOLYSIS; CHOLANIC ACID-DERIVATIVES; C-20 ALLYLIC CARBONATES; NATURAL PRODUCT OSW-1; SIGMATROPIC REARRANGEMENTS; STEREOCONTROLLED SYNTHESIS; STEREOSPECIFIC GENERATION; IONIC HYDROGENATION; EFFICIENT SYNTHESIS; VINYL IODIDES;
D O I：
10.1055/s-0029-1217521
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Stereoselective construction of steroidal side chain at C-20 having 'natural' configuration using 16-dehydropregnalone acetate (16-6PA) as a starting material has been carried out. Palladium-catalyzed carbon-carbon bond-forming Heck reaction between C-20 vinyl iodide with methyl acrylate and transfer hydrogenation with triethylsilane and Pd/C are the key steps for stereoselective side-chain synthesis.
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页码：2005 / 2009
页数：5
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