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Synthesis of (+/-)-deoxysymbioimine using an intramolecular Diels-Alder reaction with an N-alkoxycarbonyl 2,3-dihydropyridinium cation as the dienophile
Journal article   Peer reviewed

Synthesis of (+/-)-deoxysymbioimine using an intramolecular Diels-Alder reaction with an N-alkoxycarbonyl 2,3-dihydropyridinium cation as the dienophile

Barry B Snider and Qinglin Che
Angewandte Chemie (International ed.), Vol.45(6), pp.932-935
01/30/2006
DOI: https://doi.org/10.1002/anie.200503467
PMID: 16385594

Abstract

Animals Indicators and Reagents Cations Heterocyclic Compounds, 3-Ring - chemical synthesis Dinoflagellida - chemistry Pyridinium Compounds - chemistry Alkylation Aldehydes - chemistry
Three rings: Treatment of an N‐2,2,2‐trichloroethoxycarbonyl (Troc)‐substituted tetrahydropyridinol (1) with BF3⋅Et2O in CH2Cl2 gave a tricyclic adduct 2 (31 % yield) through an intramolecular Diels–Alder reaction. Reduction with zinc gave deoxysymbioimine (3), a potential antiresorptive and anti‐inflammatory drug.

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