A short biomimetic synthesis of the meroterpenoids guajadial and psidial A.
The biosynthesis of the meroterpenoid guajadial was previously hypothesized to occur via a hetero-Diels-Alder reaction between caryophyllene and an o-quinone methide. This hypothesis has been verified via the biomimetic synthesis of guajadial and psidial A in an aqueous three-component coupling reaction, between caryophyllene, benzaldehyde, and diformylphloroglucinol.
Department of Chemistry, Chemistry Research Laboratory, University of Oxford, 12 Mansfield Road, Oxford, OX1 3TA, United Kingdom.
Andrew L
AL
Lawrence
Robert M
RM
Adlington
Jack E
JE
Baldwin
Victor
V
Lee
Jessica A
JA
Kershaw
Amber L
AL
Thompson
D032701:Biomimetics; D008958:Models, Molecular; D008968:Molecular Conformation; D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D013729:Terpenes / Q000138:chemical synthesis* / Q000737:chemistry
D012717:Sesquiterpenes; D013729:Terpenes; C525798:guajadial; C547338:psidial A