Total synthesis of the neotropical poison-frog alkaloid (-)-205B

被引:63
作者
Smith, AB [1 ]
Kim, DS
机构
[1] Univ Penn, Dept Chem, Monell Chem Senses Ctr, Philadelphia, PA 19104 USA
[2] Univ Penn, Res Struct Matter Lab, Philadelphia, PA 19104 USA
[3] Univ Penn, Res Struct Matter Lab, Philadelphia, PA 19104 USA
关键词
D O I
10.1021/ol0510264
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A stereocontrolled total synthesis of the neotropical poison-frog alkaloid (-)-205B (1) has been achieved, employing a dithiane three-component linchpin coupling, a one-pot sequential construction of the embedded indolizidine ring, and ring-closing metathesis (RCM) to arrive at the novel 8b-azaacenaphthylene ring system comprising the alkaloid. The synthesis proceeded with a longest linear sequence of 19 steps, affording (-)-1 in 5.6% overall yield.
引用
收藏
页码:3247 / 3250
页数:4
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