title: Total synthesis of vinigrol.
abstract: The longstanding challenge posed by the complex diterpene vinigrol has been answered for the first time. The notorious difficulty in synthesizing vinigrol stems from its unprecedented decahydro-1,5-butanonaphthalene ring system, eight contiguous stereocenters, and highly congested functionality. This Communication delineates a stereocontrolled 23-step route to vinigrol that is scalable (>5 g prepared of a late-stage intermediate), minimally reliant on protecting group chemistry, and facilitated by a number of unique and chemoselective transformations.
authors.affiliation: Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.
authors.forename: Thomas J
authors.initials: TJ
authors.lastname: Maimone
authors.forename: Jun
authors.initials: J
authors.lastname: Shi
authors.forename: Shinji
authors.initials: S
authors.lastname: Ashida
authors.forename: Phil S
authors.initials: PS
authors.lastname: Baran
mesh_terms: D018360:Crystallography, X-Ray; D004224:Diterpenes / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D004224:Diterpenes; C055112:vinigrol