357436-25-0Relevant articles and documents
Studies on Taxol biosynthesis: preparation of taxadiene-diol and triol derivatives by deoxygenation of taxusin
Li, Hui,Horiguchi, Tohru,Croteau, Rodney,Williams, Robert M.
, p. 6561 - 6567 (2008)
The putative Taxol biosynthesis metabolites, taxa-4(20),11(12)-diene-5α,13α-diol (7), taxa-4(20),11(12)-diene-5α,9α,13α-triol (9), and taxa-4(20),11(12)-diene-5α,10β,13α-triol (10), have been prepared by Barton deoxygenation of the C-9 and C10-hydroxyl groups of protected derivatives of taxusin, a major taxoid metabolite isolated from Yew heart wood. The synthetic protocol devised is amenable for the preparation of isotopically labeled congeners that will be useful to probe further intermediate steps in the biosynthesis of Taxol.
Two-phase synthesis of (-)-taxuyunnanine D
Wilde, Nathan C.,Isomura, Minetaka,Mendoza, Abraham,Baran, Phil S.
supporting information, p. 4909 - 4912 (2014/04/17)
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.
