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Synthesis of Bis(indole) Alkaloids from Arundo donax: The Ynindole Diels–Alder Reaction, Conformational Chirality, and Absolute Stereochemistry
Author(s) -
Chen Jingjin,
Ferreira Andrew J.,
Beaudry Christopher M.
Publication year - 2014
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201407336
Subject(s) - arundo donax , racemization , chemistry , chirality (physics) , atropisomer , indole test , stereochemistry , absolute configuration , enantiomer , enantioselective synthesis , diels–alder reaction , organic chemistry , catalysis , nambu–jona lasinio model , chiral symmetry breaking , physics , quantum mechanics , quark , ecology , biofuel , biology
Bis(indole) alkaloids from Arundo donax were synthesized using the first ynindole Diels–Alder reaction. The alkaloids are chiral, having stable enantiomeric conformations with half‐lives of racemization of t 1/2 =4150–25100 seconds at room temperature. Their absolute stereochemistry was determined using the exciton chirality method.