ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
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.
Additional Material:
2 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19900730806
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