From silphinenes to penifulvins: a biomimetic approach to penifulvins B and C.
The biomimetic total synthesis of penifulvins B and C uses a meta-photocycloaddition as a key step which gives rapid access to the fenestrane-type carboskeleton with control of an onring quaternary stereocenter. The route is concise, stereocontrolled, scaleable, and flexibile and requires only one protecting group.
Gaich
Tanja
T
University of Vienna, Institute of Organic Chemistry, Wahringerstrasse 38, A-1090 Vienna, Austria. tgaich@scripps.edu
Mulzer
Johann
J
D032701:Biomimetics; D003500:Cyclization; D008968:Molecular Conformation; D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D012717:Sesquiterpenes; C547495:penifulvin B; C547496:penifulvin C