Perilla ketone, synthesis

Perilla ketone — see Ketone, 3-furyl isopentyl Perillene synthesis, 4, 668 Perinones, 1, 327, 337 Periodinane, bromo-synthesis, 1, 571 Periodinane, difluoro-reactions, 1, 571 Periodinanes cyclic... 

Perilla Ketone. l-(3-Furanyl)-4-methyl-l-penta-none l-(3-furyl)-4-meihyl-l-pentanone 0-turyl isoamyt ketone. C HmO, mol wt 166.22. C 72.26%. H 8.49%. O 19.25%. Potent pulmonary edcmatogenjc agent in animals. Isoln from the mint plant, Perilla fruteseens Britton, Labi-atae, and structure R. Goto, J. Pharm. Soc. Japan 57, 77 (1937). Synthesis T. Matsuura, Bull Chem. Soc, Japan 30, 430 (1957) K. Rondo, M. Matsumoto, Tetrahedron Letters 1976, 4363 T. Kitamura et of., Synth. Common. 7, 521 (1977) K. Inomata et al, Chem. Letters 1979, 709. Potent lung toxin implicated in emphysema of grazing cattle B. I. Wilson et al. Science 197, 573 (1977). 

Epoxidation and dehydration led to 3,4-epoxycyclohexene which, on treatment with lithium isopropenylcuprocyanide gave the alcohol 539. This was then oxidized to the ketone 538. Stevens and Albizati made 538 by addition of a methylene group to the acetyl carbonyl group in 4-acetylcyclohexanone. Somewhat more interesting is their synthesis of the (/ )-isomer of 538 from (-)-perilla alcohol (536, R = H) following Scheme 54. ... 

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