165063-59-2Relevant academic research and scientific papers
A short and enantioselective preparation of taxol A-ring fragment
Hirai, Sho,Urushizako, Naoko,Miyano, Masayuki,Fujii, Tomohiro,Nakada, Masahisa
, p. 1888 - 1892 (2013/04/23)
Two short preparations of the taxol A-ring fragment are described: one via organocatalyzed α-aminoxylation and the other via Sharpless asymmetric dihydroxylation (SAD). The former approach affords the A-ring fragment in 10 steps, and the latter approach involves eight steps to afford the new A-ring fragment in 91% ee, which is made enantiomerically pure through recrystallization. The new A-ring fragment bearing a bromoalkene is confirmed to be useful to form the carbocyclic eight-membered ring of a taxol model compound by palladium-catalyzed intramolecular alkenylation. The preparation of the new A-ring fragment will be beneficial for the total synthesis of taxol as well as other natural products.
Stereocontrolled syntheses of C-aryl taxanes by intramolecular Heck olefination. Novel instances of diastereofacial guidance by proximal coordination
Young, Wendy B.,Masters, John J.,Danishefsky, Samuel
, p. 5228 - 5234 (2007/10/02)
Stereospecific syntheses of baccatin III constructs bearing an aromatic C-ring (2a and 2b) have been demonstrated. A key step involves the use of an intramolecular Heck olefination reaction to form the C10-C11 bond. Novel stereospeci
