359014-30-5Relevant academic research and scientific papers
Probing the SAR of dEpoB via chemical synthesis: A total synthesis evaluation of C26-(1,3-dioxolanyl)-12,13-desoxyepothilone B
Chappell, Mark D.,Harris, Christina R.,Kuduk, Scott D.,Balog, Aaron,Wu, Zhicai,Zhang, Fei,Lee, Chul Bom,Stachel, Shawn J.,Danishefsky, Samuel J.,Chou, Ting-Chao,Guan, Yongbiao
, p. 7730 - 7736 (2002)
A practical total synthesis of 26-(1,3-dioxolanyl)-12,13-desoxyepothilone B (26-dioxolanyl dEpoB) was accomplished in a highly convergent manner. A novel sequence was developed to produce the vinyl iodide segment 17 in high enantiomeric excess, which was used in a key B-alkyl Suzuki merger. Subsequently, a Yamaguchi macrocyclization formed the core lactone, while a selective oxidation and a late stage Noyori acetalization incorporated the dioxolane functionality. Sufficient amounts of synthetic 26-dioxolane dEpoB were produced using this sequence for an in vivo analysis in mice containing xenograft CCRF-CEM tumors.
