Catalytic asymmetric total synthesis of (+)-yohimbine

Catalytic asymmetric total synthesis of (+)-yohimbine
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DOI:
10.1021/ol702781q
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发表时间:
2008-03-06
期刊:
影响因子:
5.2
通讯作者:
Jacobsen, Eric N.
Jacobsen, Eric N.
中科院分区:
化学1区
文献类型:
--
作者:
Mergott, Dustin J.;Zuend, Stephan J.;Jacobsen, Eric N.

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(+)-育亨宾的全合成经过11步反应,总收率14%。绝对构型是通过高对映选择性硫脲催化的酰基Pictet Spengler反应建立的,其余4个立构中心是在底物控制的分子内Diels-Alder反应中同时设置的。
The total synthesis of (+)-yohimbine was achieved in 11 steps and 14% overall yield. The absolute configuration was established through a highly enantioselective thiourea-catalyzed acyl-Pictet-Spengler reaction, and the remaining 4 stereocenters were set simultaneously in a substrate-controlled intramolecular Diels-Alder reaction.