title: The total syntheses of guttiferone A and 6-epi-guttiferone A.
abstract: Polyprenylated polycyclic acylphloroglucinols (PPAP) are a constantly growing class of natural products that exhibit a common bicyclo[3.3.1]nonatrione core and consist of currently more than 200 members. A subclassification among the various natural products of this class includes the position of the exocyclic acyl group, the prenylation grade of the core, and the relative configuration at C-7 within the core. About 10% of the reported structures, however, possess an additional chiral center at C-6. Herein we describe a straightforward access to guttiferone A and epi-guttiferone A, in which full control of stereoselectivity is achieved via conformational control, and a strict separation of framework decorating from framework constructing operations sets the stage for a short 13-step synthesis.
authors.affiliation: Institut für Organische Chemie, Universität Stuttgart , Pfaffenwaldring 55, DE-70569 Stuttgart, Germany.
authors.forename: Fiene
authors.initials: F
authors.lastname: Horeischi
authors.forename: Nicole
authors.initials: N
authors.lastname: Biber
authors.forename: Bernd
authors.initials: B
authors.lastname: Plietker
mesh_terms: D001577:Benzophenones / Q000138:chemical synthesis* / Q000737:chemistry; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis / Q000737:chemistry; D029760:Garcinia / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D001577:Benzophenones; D001688:Biological Products; D001643:Bridged Bicyclo Compounds; C558133:guttiferone A