Synthetic studies towards the phomactins. Concise syntheses of the tricyclic furanochroman and the oxygenated bicyclo[9.3.1]pentadecane ring systems in phomactin A

A concise synthesis of the tricyclic furanochroman unit 3 found in the PAF antagonist phomactin A (1) isolated from the marine fungus Phoma sp., is described. In complementary studies, a variety of synthetic routes towards the bicyclo[9.3.1]pentadecane ring system 4 in phomactin A were explored. The...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2003-11, Vol.1 (22), p.3917-3948
Main Authors: Foote, Kevin M, Hayes, Christopher J, John, Matthew P, Pattenden, Gerald
Format: Article
Language:English
Subjects:
Alkanes - chemistry
Ascomycota - metabolism
Chemistry, Organic - methods
Chromans - chemical synthesis
Furans - chemical synthesis
Furans - chemistry
Heterocyclic Compounds, 4 or More Rings - chemical synthesis
Heterocyclic Compounds, 4 or More Rings - chemistry
Models, Chemical
Oxygen - chemistry
Temperature
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Summary:A concise synthesis of the tricyclic furanochroman unit 3 found in the PAF antagonist phomactin A (1) isolated from the marine fungus Phoma sp., is described. In complementary studies, a variety of synthetic routes towards the bicyclo[9.3.1]pentadecane ring system 4 in phomactin A were explored. These studies culminated in a synthesis of the substituted ring system 79 containing all the carbon atoms and all the necessary oxygen centres for elaboration to phomactin A itself.
ISSN:1477-0520
1477-0539
DOI:10.1039/b307985f