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Total Synthesis of Sarpagine‐Related Bioactive Indole Alkaloids
Author(s) -
Rahman M. Toufiqur,
Deschamps Jeffrey R.,
Imler Gregory H.,
Cook James M.
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201705575
Subject(s) - indole test , total synthesis , stereospecificity , nonane , stereochemistry , chemistry , pictet–spengler reaction , ajmaline , tryptophan , alkaloid , organic chemistry , amino acid , biology , biochemistry , catalysis , neuroscience
Extension of the asymmetric Pictet–Spengler reaction to bulkier N b ‐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‐ seco talpinine 5 , dihydroperaksine 8 and deoxyperaksine 9 .