title: Two-phase synthesis of (-)-taxuyunnanine D.
abstract: The first successful effort to replicate the beginning of the Taxol oxidase phase in the laboratory is reported, culminating in the total synthesis of taxuyunnanine D, itself a natural product. Through a combination of computational modeling, reagent screening, and oxidation sequence analysis, the first three of eight C-H oxidations (at the allylic sites corresponding to C-5, C-10, and C-13) required to reach Taxol from taxadiene were accomplished. This work lays a foundation for an eventual total synthesis of Taxol capable of delivering not only the natural product but also analogs inaccessible via bioengineering.
authors.affiliation: Department of Chemistry, The Scripps Research Institute , 10550 North Torrey Pines Road, La Jolla, California 92037, United States.
authors.forename: Nathan C
authors.initials: NC
authors.lastname: Wilde
authors.forename: Minetaka
authors.initials: M
authors.lastname: Isomura
authors.forename: Abraham
authors.initials: A
authors.lastname: Mendoza
authors.forename: Phil S
authors.initials: PS
authors.lastname: Baran
mesh_terms: D000475:Alkenes / Q000138:chemical synthesis / Q000737:chemistry; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D004224:Diterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D010084:Oxidation-Reduction; D017239:Paclitaxel / Q000138:chemical synthesis / Q000737:chemistry; D020946:Taxus / Q000737:chemistry
chemical_list: D000475:Alkenes; D001688:Biological Products; D004224:Diterpenes; C093125:taxa-4(5),11(12)diene; C000597649:taxuyunnanine D; D017239:Paclitaxel