From Silphinenes to Penifulvins: A Biomimetic Approach to Penifulvins B and C

Tanja Gaich and Johann Mulzer

Org. Lett., 2010, 12 (2), pp 272–275

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.