title: Stereocontrolled Synthesis of Kalihinol C.
abstract: We report a concise chemical synthesis of kalihinol C via a possible biosynthetic intermediate, "protokalihinol", which was targeted as a scaffold en route to antiplasmodial analogs. High stereocontrol of the kalihinol framework relies on a heterodendralene cascade to establish the target stereotetrad. Common problems of regio- and chemoselectivity encountered in the kalihinol class are explained and solved.
authors.affiliation: Department of Chemistry, The Scripps Research Institute , La Jolla, California 92037, United States.
authors.forename: Christopher A
authors.initials: CA
authors.lastname: Reiher
authors.affiliation: Department of Chemistry, The Scripps Research Institute , La Jolla, California 92037, United States.
authors.forename: Ryan A
authors.identifier: 0000-0001-8353-6449
authors.initials: RA
authors.lastname: Shenvi
mesh_terms: D004224:Diterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009570:Nitriles / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013816:Thermodynamics
chemical_list: D004224:Diterpenes; D009570:Nitriles; C484758:kalihinol C