Biomimetic cycloaddition approach to tropolone natural products via a tropolone ortho-quinone methide.
[reaction: see text] A study toward a possible biomimetic hetero Diels-Alder reaction is reported between humulene and a novel tropolone ortho-quinone methide. A suitable tropolone ortho-quinone methide precursor has been prepared from 3-methyl-2-furoate. Heating the ortho-quinone methide precursor gave a tropolone ortho-quinone methide, which in the presence of humulene underwent a hetero Diels-Alder reaction to give a deoxy analogue of epolone B.
Adlington
Robert M
RM
Dyson Perrins Laboratory, University of Oxford, South Parks Road, Oxford OX1 3QY, UK.
Baldwin
Jack E
JE
Mayweg
Alexander V W
AV
Pritchard
Gareth J
GJ
D000740:Anemia / Q000188:drug therapy; D004921:Erythropoietin / Q000235:genetics; D015870:Gene Expression / Q000187:drug effects; D045563:Indolequinones; D007211:Indoles / Q000737:chemistry; D018716:Molecular Mimicry; D000081222:Monocyclic Sesquiterpenes; D011809:Quinones / Q000737:chemistry; D012717:Sesquiterpenes / Q000737:chemistry; D014334:Tropolone / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology
D045563:Indolequinones; D007211:Indoles; D000081222:Monocyclic Sesquiterpenes; D011809:Quinones; D012717:Sesquiterpenes; D004921:Erythropoietin; C068040:quinone methide; C042686:humulene; D014334:Tropolone