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

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...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 53; no. 16; pp. 3658 - 3662
Main Authors Grieco, Paul A, Parker, David T
Format Journal Article
LanguageEnglish
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(-)
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Summary: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 2.2:1. The formation of 9 and 10 is rationalized on the basis of the chair-like conformations 16 and 17 respectively. Reduction of the double bond in 9 afforded (-)-8a-epipumiliotoxin C.
Bibliography:istex:738E900991D4430288904EC8E97284930A2DD494
ark:/67375/TPS-0ZGCJHGQ-W
ISSN:0022-3263
1520-6904
DOI:10.1021/jo00251a002