115094-15-0Relevant articles and documents
Octahydroquinoline Syntesis via Immonium Ion Based Diels-Alder Chemistry: Synthesis of (-)-8a-Epipumiliotoxin C
Grieco, Paul A.,Parker, David T.
, p. 3658 - 3662 (2007/10/02)
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 affored (-)-8a-epipumiliotoxin C.