18783-45-4Relevant academic research and scientific papers
The first enantiospecific total synthesis of a C-quaternary voachalotine alkaloid, (+)-dehydrovoachalotine
Yu, Jianming,Wearing, Xiangyu Z.,Cook, James M.
, p. 3937 - 3940 (2004)
The first enantiospecific total synthesis of the indole alkaloid (+)-dehydrovoachalotine (1) has been achieved from D-(+)-tryptophan methyl ester in 28% overall yield. The formation of the prochiral quaternary carbon center at C-16 in the key intermediate (12) was realized via a Tollens reaction from Na-methylvellosimine (13) in 95% yield. This approach could also be applied to the synthesis of many other indole alkaloids that contain a quaternary carbon center at C(16).
A general strategy for the synthesis of vincamajine-related indole alkaloids: Stereocontrolled total synthesis of (+)-dehydrovoachalotine, (-)-vincamajinine, and (-)-11-methoxy-17-epivincamajine as well as the related quebrachidine diol, vincamajine diol,
Yu, Jianming,Wearing, Xiangyu Z.,Cook, James M.
, p. 3963 - 3979 (2007/10/03)
The highly convergent stereocontrolled total synthesis of (-)-vincamajinine (7), (-)-11-methoxy-17-epivincamajine (9), and the oxygen-bridged (+)-dehydrovoachalotine (22) are described. Key steps in the synthesis of 7 and 9 involved the stereospecific eno
