38990-35-1Relevant academic research and scientific papers
Total Synthesis of Sarpagine-Related Bioactive Indole Alkaloids
Rahman, M. Toufiqur,Deschamps, Jeffrey R.,Imler, Gregory H.,Cook, James M.
, p. 2354 - 2359 (2018/01/27)
Extension of the asymmetric Pictet–Spengler reaction to bulkier Nb-alkylated tryptophan derivatives resulted in an improved stereospecific access to the key bicyclo[3.3.1]nonane core of bioactive C-19 methyl substituted sarpagine/macroline/ajmaline indole alkaloids with excellent diastereoselectivity by internal asymmetric induction. Complete stereocontrol of the C-19 methyl function in either the α- or β-configuration was achieved, which enables the total synthesis of any member from this group of thirty alkaloids. We report herein, the total synthesis of macrocarpines (A-C) 1–3, talcarpine 4, N(4)-methyl-N(4),21-secotalpinine 5, dihydroperaksine 8 and deoxyperaksine 9.
An efficient synthetic pathway to the macroline-type indole alkaloids, talcarpine and alstonerine from ajmaline
Takayama, Hiromitsu,Phisalaphong, Chada,Kitajima, Mariko,Aimi, Norio,Sakai, Shin-Ichiro
, p. 1383 - 1392 (2007/10/09)
Ajmaline (6) was transformed into two macroline-related indole alkaloids, talcarpine (1) and alstonerine (2) via the common synthetic intermediate (13). The stereochemistry at C19 position in talcarpine (1) and talpinine (5) were elucidated by NOE experim
