Tetrahedron

A New Asymmetric Synthesis of (S)-Dolaphenine and Its Heteroaromatic Congeners Utilizing (+)-2-Hydroxy-3-pinanone and (−)-3-Hydroxy-2-caranone as Chiral …

N Irako, Y Hamada, T Shioiri

Index: Irako, Naoko; Hamada, Yasumasa; Shioiri, Takayuki Tetrahedron, 1995 , vol. 51, # 46 p. 12731 - 12744

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Citation Number: 47

Abstract

(+)-2-Hydroxy-3-pinanone ((+)-HyPN,(+)-2a) and (−)-3-hydroxy-2-caranone ((−) 2b) were respectively converted to the corresponding Schiff bases 18a and 18b with 1-(2 thiazolyl) methylamine (17). Alkylation followed by removal of the chiral auxiliaries (+)-2a and (−)-2b afforded (S)-dolaphenine (10) as an optically pure form. The method was applied to the asymmetric synthesis of the dolaphenine analogs 27ad.