Total Synthesis of Bacilosarcins A and B

被引:38
作者
Enomoto, Masaru [1 ]
Kuwahara, Shigefumi [1 ]
机构
[1] Tohoku Univ, Lab Appl Bioorgan Chem, Grad Sch Agr Sci, Aoba Ku, Sendai, Miyagi 9818555, Japan
关键词
alkaloids; epoxidation; heterocycles; natural products; total synthesis; MICROBIAL AGENT AI-77-B; BACILLUS-PUMILUS AI-77; AMINO-ACID MOIETY; STEREOSELECTIVE-SYNTHESIS; GASTROPROTECTIVE SUBSTANCE; ALPHA; BETA-UNSATURATED ALDEHYDES; DIHYDROISOCOUMARIN MOIETY; AMADORI REARRANGEMENT; ASYMMETRIC-SYNTHESIS; ORGANIC-SYNTHESIS;
D O I
10.1002/anie.200804571
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) I want to ride my bicycle: The thermodynamic stability of nitrogen-containing heterocyclic ring systems is exploited in the first enantioselective total synthesis of bacilosarcins A and B, which has been achieved in simple two-step sequences from amicoumacin C. Bacilosarcin A incorporates a totally unprecedented heterobicyclic ring system and exhibits a remarkably potent herbicidal activity. © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:1144 / 1148
页数:5
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