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. 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.
Foote
Kevin M
KM
School of Chemistry, The University of Nottingham, University Park, Nottingham, UK NG7 2RD.
Hayes
Christopher J
CJ
John
Matthew P
MP
Pattenden
Gerald
G
D000473:Alkanes / Q000737:chemistry; D001203:Ascomycota / Q000378:metabolism; D002625:Chemistry, Organic / Q000379:methods; D002839:Chromans / Q000138:chemical synthesis*; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis* / Q000737:chemistry*; D008956:Models, Chemical; D010100:Oxygen / Q000737:chemistry*; D013696:Temperature
D000473:Alkanes; D002839:Chromans; D005663:Furans; D006576:Heterocyclic Compounds, 4 or More Rings; C491966:furanochroman; C413206:phomactin A; C033245:pentadecane; D010100:Oxygen; C039281:furan