Total synthesis of (-)-epibatidine using an asymmetric Diels-Alder reaction with a chiral N-acylnitroso dienophile

…, R Tanaka, M Naruse, C Kibayashi

Index: Aoyagi, Sakae; Tanaka, Ryuta; Naruse, Masaichi; Kibayashi, Chihiro Journal of Organic Chemistry, 1998 , vol. 63, # 23 p. 8397 - 8406

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Citation Number: 73

Abstract

An asymmetric total synthesis of (-)-epibatidine (1), isolated from the skin of the Ecuadorian poison frog, Epipedobates tricolor, of the family Dendrobatidae, has been achieved by virtue of the development of asymmetric hetero Diels-Alder (DA) cycloaddition with an N- acylnitroso dienophile bearing the optically active 8-arylmenthol as a chiral source. Thus, in situ oxidation of the hydroxamic acid ent-12f incorporating the (1 S, 2 R, 5 S)-8-(2-naphthyl ...

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