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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 international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201407336
Subject(s) - arundo donax , racemization , chirality (physics) , chemistry , indole test , absolute configuration , stereochemistry , atropisomer , enantiomer , diels–alder reaction , organic chemistry , catalysis , physics , biomass (ecology) , biology , quantum mechanics , nambu–jona lasinio model , chiral symmetry breaking , quark , agronomy
Abstract 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.