Tetrahedron p. 12731 - 12744 (1995)
Update date:2022-08-03
Topics:
Irako, Naoko
Hamada, Yasumasa
Shioiri, Takayuki
(+)-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 27a-d.
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