NOVEL C-9 AND C-11 HYDROCARBONS FROM THE BROWN ALGA CUTLERIA-MULTIFIDA .6. SIGMATROPIC AND ELECTROCYCLIC REACTIONS IN NATURE

被引:16
作者
KEITEL, J
FISCHERLUI, I
BOLAND, W
MULLER, DG
机构
[1] UNIV KARLSRUHE,INST ORGAN CHEM,RICHARD WILLSTATTER ALLEE 2,W-7500 KARLSRUHE,GERMANY
[2] UNIV CONSTANCE,FAK BIOL,W-7750 CONSTANCE,GERMANY
关键词
D O I
10.1002/hlca.19900730806
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
In addition to the known C11H16 hydrocarbons multifidene (4), aucantene (2), and ectocarpene (5), the marine brown alga Cutleria multifida produces trace amounts of the C9H12 hydrocarbon 7‐melhylcycloocta‐1,3,5‐triene (8) and its valence tautomer 7‐methylbicyclo[4.2.0]octa‐2,4‐diene, A second novel C9H12 hydrocarbon is 6‐vinyicyclo‐hepta‐1,4‐diene (9), a lower homologue of ectocarpene (5). Among the C11H16 hydrocarbons, 7‐((1E/Z)‐prop‐l‐enyl)cycloocta‐1,4‐diene (10/11) is found for the first time. The structure of all new products is confirmed by synthesis and spectroscopic data. The biosynthesis of the new hydrocarbons 8–11 is obviously linked to the pathways which lead to the major products giffordene (7), (6S)‐ectocarpene ((6S)‐5), and (4R,5R)‐aucantene ((4R,5R)‐2). Consecutive reactions of certain thermolabile primary products proceed via electrocyclic ring closure, 3,3‐sigmatropic rearrangement, or a 1,7‐sigmatropic H‐shift. Copyright © 1990 Verlag GmbH & Co. KGaA, Weinheim
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页码:2101 / 2112
页数:12
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