BIOSYNTHESIS OF ALGAE PHEROMONES .4. PERICYCLIC-REACTIONS IN NATURE - SPONTANEOUS COPE REARRANGEMENT INACTIVATES ALGAE PHEROMONES

被引:22
作者
BOLAND, W [1 ]
POHNERT, G [1 ]
MAIER, I [1 ]
机构
[1] UNIV KONSTANZ,FAK BIOL,W-7750 CONSTANCE,GERMANY
来源
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH | 1995年 / 34卷 / 15期
关键词
BIOSYNTHESES; COPE REARRANGEMENTS; PERICYCLIC REACTIONS; PHEROMONES;
D O I
10.1002/anie.199516021
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A pheromone roughly 100 times more effective than cyclohepta‐1,4‐diene 2 (R = C2H5, ectocarpene) is its biosynthetic precursor 1. This thermally labile cis‐disubstituted cyclopropane is the actual signaling agent of the marine brown algae Ectocarpus siliculosus. The [3,3]sigmatropic rearrangement of 1 giving 2 (t1/2 = 21 min at 18°C) is the fastest known reaction for the spontaneous inactivation of a pheromone. (Figure Presented.) Copyright © 1995 by VCH Verlagsgesellschaft mbH, Germany
引用
收藏
页码:1602 / 1604
页数:3
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