6533b7dafe1ef96bd126f418

RESEARCH PRODUCT

Photochemical Approaches to the Bilobalide Core

Jens EmsermannTill Opatz

subject

biology010405 organic chemistryChemistryGinkgo bilobaStereochemistryGinkgoOrganic ChemistryTotal synthesis010402 general chemistryPhotochemistrybiology.organism_classificationSesquiterpene01 natural sciences0104 chemical scienceschemistry.chemical_compoundBilobalideOrganic chemistryPhysical and Theoretical Chemistry

description

Bilobalide is a tetracyclic sesquiterpene containing three contiguous γ-lactone rings and an unusual tert-butyl group, which is found in the leaves of the ginkgo tree (Ginkgo biloba). Three different photochemical approaches towards bilobalide's unique skeleton are presented. A meta photocycloaddition, a [2 + 2] photocycloaddition, and a Paterno–Buchi-reaction were chosen as the respective key steps.

https://doi.org/10.1002/ejoc.201700461