Octahydroquinoline synthesis via immonium ion based Diels-Alder chemistry. Synthesis of (-)-8a-epipumiliotoxin C

• Published in: Journal of organic chemistry Vol. 53; no. 16; pp. 3658 - 3662
• Main Authors: Grieco, Paul A, Parker, David T
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 01.08.1988; Amer Chemical Soc
• Subjects: Chemistry; Chemistry, Organic; Exact sciences and technology; Heterocyclic compounds; Heterocyclic compounds with only one n hetero atom and condensed derivatives; Organic chemistry; Physical Sciences; Preparations and properties; Science & Technology; Intramolecular reaction; Nitrogen heterocycle; Iminium compounds; Epimer; Diels Alder addition; Chemical reduction; Toxin; Alkaloid; Bicyclic compound; Conjugated dienic compound; Ammonium Chlorides; Conformation; Enantiomer(-)

A total synthesis of (-)-8a-epipumiliotoxin C has been developed which features an intramolecular immonium ion based Diels-Alder reaction. Cyclocondensation of the immonium ion 8 derived from optically pure aldehyde 2 and ammonium chloride provided two octahydroquinolines 9 and 10, in a ratio of 2.2...