Construction of Enantiopure Taxoid and Natural Product-like Scaffolds Using a C-C Bond Cleavage/Arylation Reaction.
An approach to construct enantiopure complex natural product-like frameworks, including the first reported synthesis of a C17 oxygenated taxoid scaffold, is presented. A palladium-catalyzed C-C activation/cross-coupling is utilized to access these structures in a short sequence from (+)-carvone; the scope of this reaction is explored.
Department of Chemistry, University of California-Berkeley , Berkeley, California 94720, United States.
Manuel
M
Weber
Department of Chemistry, University of California-Berkeley , Berkeley, California 94720, United States.
Kyle
K
Owens
Department of Chemistry, University of California-Berkeley , Berkeley, California 94720, United States.
Ahmad
A
Masarwa
Department of Chemistry, University of California-Berkeley , Berkeley, California 94720, United States.
Richmond
R
Sarpong
D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D000081005:Cyclohexane Monoterpenes; D015394:Molecular Structure; D039821:Monoterpenes / Q000737:chemistry; D010165:Palladium / Q000737:chemistry; D013237:Stereoisomerism; D043823:Taxoids / Q000138:chemical synthesis* / Q000737:chemistry
D001688:Biological Products; D000081005:Cyclohexane Monoterpenes; D039821:Monoterpenes; D043823:Taxoids; D010165:Palladium; C006923:carvone