By K H Overton
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Morris and A. M. S. Perkin II, 1975, 734. R. Haseltine, E. Huang, K. Ranganayakulu, and T. S. Sorensen, Canad. J. , 1975,53, 1056. R. P. Haseltine and T. S. Sorensen, Canad. J. , 1975, 53, 1067. 272Acetolysis of the endo- and eno-ethynyl ethers (179) to yield (ISO), which is further transformed to the acetate (18l),exhibits a ratio k,,, : kendoof 5 : Base-catalysed rearrangement of the anhydride (182) to the acid (183) involves C-8 methyl migration,274 and HBr elimination from em-2-bromoapobornanecarboxylic acid (184; R = H) proceeds by y-elimination whereas the corresponding methyl ester gives p-elimination in addition; other esters (184; R = Et, Pr, or Bu) give only p - e l i m i n a t i ~ nBrown .
Chem. , 1974,856. J. H. Babler, Tetrahedron Letters, 1975, 2045. B. M. Trost and D. E. Keeley, J. Org. , 1975,40, 2013. 22 Terpenoids and Steroids synthesized conventionally from the corresponding ci~-bicyclo[3,2,0]heptanone, yields the keto-acid (76),'63 which has previously been converted into grandisol(73). (73) (74) (75) (76) A second synthesis of chiral grandisol (73) from trans-pinan-2P-01 (77; X = H) derived from (-)-P-pinene, as shown in Scheme 8, involves the useful photochemical $-t 4 l-lll,+b (77) (73) t o 4-5 V-Vll,I'-.
Y-fi HO (254) \ 353 354 35s C5Hll (255) C5HI 1 S. Tori;, K. Uneyama, and M. Isihara, J. Org. , 1974, 39, 3645. L. Hanus and Z. Krejci, Acta Univ. , Fac. , 1974, 71, 239. R. A. Archer in 'Annual Reports in Medicinal Chemistry', ed. R. V. Heinzelman, Academic Press, New York, 1974, Vol. 9. J. Friedrich-Fiechtl and G. Spiteller, Tefrabedron, 1975, 31. 479. 49 Monoterpenoids The phenolic hydroxy-group in THC's is important to their pharmacological and analgesic properties may be due to metabolism to 7-hydroxyderivatives (using normal monoterpenoid n ~ m b e r i n g ) .