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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.

SUBMITTER: Wilde NC

PROVIDER: S-EPMC3985808 | biostudies-literature | 2014 Apr

REPOSITORIES: biostudies-literature

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Two-phase synthesis of (-)-taxuyunnanine D.

Wilde Nathan C NC Isomura Minetaka M Mendoza Abraham A Baran Phil S PS

Journal of the American Chemical Society 20140319 13

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 tot ...[more]

PMID: 24625050

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