163594-75-0Relevant articles and documents
Studies on the Biosynthesis of Taxol: Total Synthesis of Taxa-4(20),11(12)-diene and Taxa-4(5),11(12)-diene. The First Committed Biosynthetic Intermediate
Rubenstein, Steven M.,Williams, Robert M.
, p. 7215 - 7223 (1995)
The total synthesis of taxa-4(20),11(12)-diene and taxa-4(5),11(12)-diene is described.
Total synthesis of taxane terpenes: Cyclase phase Dedicated to Professor Melanie S. Sanford on the occasion of her receipt of the Tetrahedron Young Investigator Award
Ishihara, Yoshihiro,Mendoza, Abraham,Baran, Phil S.
, p. 5685 - 5701 (2013/07/19)
A full account of synthetic efforts toward a lowly oxidized taxane framework is presented. A non-natural taxane, dubbed 'taxadienone', was synthesized as our first entry into the taxane family of diterpenes. The final synthetic sequence illustrates a seven-step, gram-scale, and enantioselective route to this tricyclic compound in 18% overall yield. This product was then modified further to give (+)-taxadiene, the lowest oxidized member of the taxane family of natural products.
Stereochemistry of the macrocyclization and elimination steps in taxadiene biosynthesis through deuterium labeling
Jin, Qingwu,Williams, David C.,Hezari, Mehri,Croteau, Rodney,Coates, Robert M.
, p. 4667 - 4675 (2007/10/03)
Taxadiene synthase catalyzes the cyclization of (E,E,E)-geranylgeranyl diphosphate (GGPP) to taxa-4(5),11(12)-diene (Scheme 1, 5 → 2) as the first committed step of Taxol biosynthesis. Deuterated GGPPs labeled stereospecifically at C-1, C-4, and C-16 were