A Review of the literature published between September and by K H Overton

By K H Overton

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Kupletskaya, Zhur. , 1973,43, 926, 930. V. M. Potapov, G. V. Panova, and N. K. Vikulova, Zhur. , 1973,43,939. C. K. Johnson and C. J . Collins, J . Amer. Chem. ,1974, 96, 2514; C. J. Collins, C. K. Johnson, and V. F. , p. 2524. G . A. Olah and G. Liang, J. Amer. Chem. ,1974, 96, 189. Y . Castanet, F. Petit, and M. Evrard, Bull. chim. France, 1974, 1097. C. J. Collins and M. H. Lietzke, J. Amer. Chem. ,1973, 95, 6842. 223 Re-examination of the thermal decomposition of borneol and isoborneol p-nitrobenzoates and urethanes has led to the detection of a small amount of pinene besides the known tricyclene, camphene, etc.

Ac,O. 130 " C ; v, Reagents: i, VO(acac),-Bu'OOW; HCIO,. 9 Both compounds co-occur with the intercsting e' 1 2 metabolite furocaespitane (17)*' in the marine alga Laurencia caespitosa Larnx. The spectroscopic properties reported" for furocaespitane are also consistent with the alternative structure (18). Br' &c, u%cl B%Br C1 Br Rr (14) (15) (16) Br (17) A. G . Gonzfilez, J. Darias, and J. D. , p. 3625. '" A A (19) R = CHO (20) R = CHZOH (21) Alternative synthetic routes to ( & )-ar-turmerone (22)' ' (Scheme 3), ( k )-a-atlantone (23)12(Scheme 4),and (+)-(E)-nuciferol (24)13have been reported.

1974, 61, 117. Chem. and Eng. News, 1974, Aug. 26, p. 6. C. A. L. Bercht, R. J. J. C. Lousberg, F. J. E. M. Kiippers, and C. A. Salemink, Phytochemistry, 1974, 13,619. E. Small and H . D. Beckstead, Nature, 1973, 245, 147. Perez-Reyes, M. C. Timmons, K. H. Davis, and E. M. Wall, Experientia, 1973, 29, 1368. 323 It is possible to predict the retention times of the cannabinoids from those of substituted r e s o r ~ i n o l sMass . r. spectra of many hydroxylated cannabinoids have been quoted to facilitate the identification of In the mass spectrum of A'-THC, it seems that double-bond isomerization to A6-THC and transfer of the phenolic proton are important before f r a g m e n t a t i ~ n .

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