217448-33-4Relevant academic research and scientific papers
Enantiospecific total synthesis of (-)-(E)16-epiaffinisine, (+)-(E)16-epinormacusine B, and (+)-dehydro-16-epiaffinisine as well as the stereocontrolled total synthesis of alkaloid G
Yu, Jianming,Wang, Tao,Wearing, Xiangyu Z.,Ma, Jun,Cook, James M.
, p. 5852 - 5859 (2003)
An efficient strategy is described for the total synthesis of the sarpagine-related indole alkaloids (-)-(E)16-epiaffinisine (1), (+)-(E)16-epinormacusine B (2), and (+)-dehydro-16-epiaffinisine (4). A key step employed the chemospecific and regiospecific
Stereocontrolled Total Synthesis of Alkaloid G via the Oxy-anion Cope Rearrangement and Improved Total Synthesis of (+)-Ajmaline
Wang, Tao,Xu, Qingge,Yu, Peng,Liu, Xiaoxiang,Cook, James M.
, p. 345 - 348 (2007/10/03)
(Matrix Presented) The oxy-anion Cope rearrangement followed by protonation of the enolate which resulted under conditions of kinetic control has been employed to generate the key asymmetric centers at C(15), C(16), and C(20) in alkaloid G (1) and (+)-ajm
General approach for the synthesis of ajmaline/sarpagine indole alkaloids: Enantiospecific total synthesis of (+)-ajmaline, alkaloid G, and norsuaveoline via the asymmetric Pictet-Spengler reaction
Li, Jin,Wang, Tao,Yu, Peng,Peterson,Weber,Soerens,Grubisha,Bennett,Cook
, p. 6998 - 7010 (2007/10/03)
A general approach (oxyanion-Cope strategy) for the synthesis of sarpagine/ajmaline indole alkaloids has been developed. (+)-Ajmaline 1 and alkaloid G 2 as well as norsuaveoline 3 have been synthesized from D-(+)-tryptophan in enantiospecific fashion via
The enantiospecific total synthesis of norsuaveoline
Wang, Tao,Yu, Peng,Li, Jin,Cook, James M.
, p. 8009 - 8012 (2007/10/03)
Norsuaveoline la has been synthesized enantiospecifically in 28% overall yield from commercially available D-(+)-tryptophan methyl ester via the asymmetric Pictet-Spengler reaction and a stereocontrolled oxy-anion Cope rearrangement as key steps.
