Synthesis of the erythrina alkaloid 3-demethoxyerythratidinone. Novel acid-induced rearrangements of its precursors.
[reaction: see text] A new strategy for the synthesis of 3-demethoxyerythratidinone has been developed and is based on an extraordinarily facile intramolecular Diels-Alder reaction of a 2-imido-substituted furan. During the course of the synthesis, several novel acid-induced rearrangement reactions were encountered.
Wang
Qiu
Q
Department of Chemistry, Emory University, Atlanta, Georgia 30322, USA.
Padwa
Albert
A
D002384:Catalysis; D004895:Erythrina / Q000737:chemistry*; D007202:Indicators and Reagents; D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure
C514302:3-demethoxyerythratidinone; D007202:Indicators and Reagents; D026121:Indole Alkaloids