By K H Overton
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Walkowicz, C. Walkowicz, and H. Kuczynski, Bull. Acad. polon. , 1973, 21, 343. 311 3'2 313 3'4 F. Bondavalli, P. Schenone, and M. Longobardi, Farmaco, Ed. , 1974, 29,48. M. G. Peter, G. Snatzke, F. Snatzke, K. N. Nagarajan, and H. Schmid, Helv. Acta, 1974, 57, 32. S. Wakayarna, S. Narnba, K. Hosoi, and M . Ohno, Bull. Chrrn. Soc. Japan, 1973, 46, 3183; S. Wakayarna and S. , 1974, 47, 1293. S. Akutagawa and S. Watanabe, Jap. , 61 46811973. 62 1 three steps 8 Cannabinoids and other Phenolic Monoterpenoids Marihuana chemistry3l 6 and the syntheses of tetrahydrocannabinol (THC), its metabolites, and the a z a - a n a l ~ g u e s ~ have ’ ~ been reviewed.
Soc. chim. France, 1974, 888; cJ notes by these authors: Tetrahedron Letters, 1971. 1049; Compt. , 1971, 272, C , 417; and the (unquoted) work of M. Narayanaswamy, V. M. Sathe, and A. S. Rao, Chem. , 1969,921. l E 7M. Santelli and M. Bertrand, Bull. chim. France, 1973, 2326; B. Ragonnet, M. Santelli, and M. , p. 3119. C. H. Brieskorn and H. H. Frohlich, Arch. , 1973, 306, 641. 19’ V. V. Bazyl’chik, I. I. Bardyshev, N. M. Ryabushkina, N . P. Polyakova, and P. I. Fedorov, Vestsi Akad. Navuk Belarusk.
Brieskorn and H. H. Frohlich, Arch. , 1973, 306, 641. 19’ V. V. Bazyl’chik, I. I. Bardyshev, N. M. Ryabushkina, N . P. Polyakova, and P. I. Fedorov, Vestsi Akad. Navuk Belarusk. S . S . R . , Ser. khim. Navuk, 1973, 104. J. Ficini and A. M. Touzin, Tetrahedron Letters, 1974, 1447. ' 94 Some transformations of P-pyronene (146), available from pyrolysis of a-pinene, are described (Scheme 14),in the course of which dehydro-1,4-cineol(l48) is quoted [the analogous oxide (149) HO R = (147) R = (146) Reagents: i, hv, O,-sensitizer; ii, LiAlH,; iii, HCrO, (two-phase); iv, NaBH,; vi, monoperphthalic acid.