A new and efficient method for o-quinone methide intermediate generation: application to the biomimetic synthesis of the benzopyran derived natural products (+/-)-lucidene and (+/-)-alboatrin.
Lucidene and alboatrin are complex benzopyran derived natural products. A key step in their biogenesis may involve a hetero Diels-Alder cycloaddition between an o-quinone methide intermediate with a simple, or activated tri-substituted olefin. Experimental evidence is provided to support this hypothesis, with the biomimetic synthesis of both (+/-)-lucidene and (+/-)-alboatrin successfully achieved using a new and efficient method for o-quinone methide generation.
Rodriguez
Raphaël
R
The Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford, UKOX1 3TA.
Moses
John E
JE
Adlington
Robert M
RM
Baldwin
Jack E
JE
D000475:Alkenes / Q000737:chemistry; D001578:Benzopyrans / Q000737:chemistry*; D016227:Benzoquinones / Q000138:chemical synthesis*; D001688:Biological Products / Q000138:chemical synthesis*; D032701:Biomimetics; D003500:Cyclization; D045563:Indolequinones / Q000737:chemistry*; D008956:Models, Chemical; D011809:Quinones / Q000138:chemical synthesis*; D012717:Sesquiterpenes / Q000138:chemical synthesis*
D000475:Alkenes; D001578:Benzopyrans; D016227:Benzoquinones; D001688:Biological Products; D045563:Indolequinones; D011809:Quinones; D012717:Sesquiterpenes; C504944:alboatrin; C410427:lucidene; C068040:quinone methide