16101-12-5Relevant academic research and scientific papers
Unusual spirocyclic macroline alkaloids, nitrogenous derivatives, and a cytotoxic bisindole from Alstonia
Kam, Toh-Seok,Choo, Yeun-Mun,Komiyama, Kanki
, p. 3957 - 3966 (2004)
The bark extract of the Malayan A. macrophylla provided several novel indoles with unprecedented carbon skeletons, an unusual nitrogenous compound, a cytotoxic bisindole, several new macroline alkaloids, in addition to other known alkaloids. The structures of the new compounds were established by spectroscopic analysis.
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.
