221649-16-7Relevant articles and documents
The effect of DMSO on the borohydride reduction of a cyclohexanone: A formal enantioselective synthesis of (+)-epibatidine
Barros, M. Teresa,Maycock, Christopher D.,Ventura, M. Rita
, p. 557 - 560 (1999)
An asymmetric synthesis of (+)-epibatidine is described which uses the increased stereoselectivity of a borohydride reduction induced by the presence of DMSO.
Enantioselective α-arylation of cyclohexanones with diaryl iodonium salts: Application to the synthesis of (-)-epibatidine
Aggarwal, Varinder K.,Olofsson, Berit
, p. 5516 - 5519 (2007/10/03)
(Chemical Equation Presented) Short cut: Direct asymmetric α-arylation of prochiral ketones has been effected using chiral lithium amide bases and diaryl iodonium salts. The methodology has been employed in a short total synthesis of the alkaloid (-)-epibatidine (see scheme).
Approaches to the synthesis of (+)- and (-)-epibatidine
Barros, M. Teresa,Maycock, Christopher D.,Ventura, M. Rita
, p. 166 - 173 (2007/10/03)
Synthetic approaches to the powerful analgesic alkaloids (+)- and (-)-epibatidine are described. The starting material employed was natural (-)-quinic acid from which chiral enones and α-iodoenones were prepared. Stille coupling afforded suitable substrat