Total synthesis of (-)-kendomycin exploiting a petasis-ferrier rearrangement/ring-closing olefin metathesis synthetic strategy

被引:59
作者
Smith, AB [1 ]
Mesaros, EF
Meyer, EA
机构
[1] Univ Penn, Monell Chem Senses Ctr, Dept Chem, Philadelphia, PA 19104 USA
[2] Univ Penn, Res Struct Matter Lab, Philadelphia, PA 19104 USA
关键词
D O I
10.1021/ja051420x
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The total synthesis of (-)-kendomycin (1), a novel macrocyclic polyketide with antibacterial and antitumor activity, was achieved in 21 steps (longest linear sequence) exploiting an effective Petasis-Ferrier union/rearrangement tactic to construct the tetrahydropyran ring, a ring-closing metathesis to generate the macrocycle, and a biomimetic quinone-methide-lactol assembly. Copyright © 2005 American Chemical Society.
引用
收藏
页码:6948 / 6949
页数:2
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