Photochemical Relationships in Sacoglossan Polypropionates
Cyercene A (7) has been synthesized and converted to placidene A (3) and isoplacidene A (8) through photoisomerization with sunlight. Hydroperoxide 4, isolated form Placida dendritica, was synthesized both by singlet oxygenation of cyercene A using Rose Bengal and through the irradiation of cyercene...
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Published in | Journal of natural products (Washington, D.C.) Vol. 68; no. 4; pp. 481 - 486 |
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Main Authors | , |
Format | Journal Article |
Language | English |
Published |
WASHINGTON
American Chemical Society
01.04.2005
Amer Chemical Soc American Society of Pharmacognosy |
Subjects | |
Online Access | Get full text |
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Summary: | Cyercene A (7) has been synthesized and converted to placidene A (3) and isoplacidene A (8) through photoisomerization with sunlight. Hydroperoxide 4, isolated form Placida dendritica, was synthesized both by singlet oxygenation of cyercene A using Rose Bengal and through the irradiation of cyercene A alone in aerobic solution. The observation that hydroperoxide 4 could be made by singlet oxygenation of cyercene A and that this occurs when cyercene A alone is irradiated supported the hypothesis that γ-pyrones may act as triplet sensitizers. This was confirmed using cyercene A and a model γ-pyrone to sensitize the photooxidation of n-butyl sulfide. The biosynthetic implications of these observations for Sacoglossan polypropionates are discussed. |
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Bibliography: | istex:3206D11C71321FAA14DAE6B417CEEA9BE414388C ark:/67375/TPS-9XGX5NRQ-4 Medline NIH RePORTER ObjectType-Article-2 SourceType-Scholarly Journals-1 ObjectType-Feature-1 content type line 23 ObjectType-Article-1 ObjectType-Feature-2 |
ISSN: | 0163-3864 1520-6025 |
DOI: | 10.1021/np049607+ |