By Royal Society Of Chemistry
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Additional resources for Alkaloids (v. 9)
Sellers, K. Mascaro, and H. G. Floss, J. Amer. Chem. ,1977, 99, 273; R. B. Herbert, in ref. 8, p. 23; in ref. 7, p. 16; in ref. 3, p. 10; and refs. cited. 13' The synthesis of dimethylallyltryptophan (132) by a crude extract of Claviceps purpurea from tryptophan and dimethylallyl pyrophosphate recorded earlier13' has been reported again r e ~ e n t 1 y . In l ~ addition ~ to (132), the formation of (133) was observed. (The latter compound, with unspecified stereochemistry around the double bond, has also been isolated from a C.
Just and G. P. Donnini, Canad. J. , 1977, 55, 2998. R. A. Olofson, R. C. Schnur, L. Bunes, and J . P. Pepe, Tetruhedron Letters, 1977, 1567. V. I. Stenberg, N. K. Narain, S. P. Singh, and S. S . Parmar, J. , 1976, 13,363. 0. Kovacs, G. Fodor, and I. Weisz, Helv. Chim. Actu, 1954, 37, 905. The Alkaloids 50 Teloidine + Demethylation of cocaine was also achieved by 2,2,2-trichloroethyl chlorof ~ r m a t e ~and ~ ’ ~reduction, * or by using27 Ollofson’s reagent,24 vinyl chloroformate, [via (26)] and subsequent cleavage27of the vinyloxycarbonyl group with mild acid.
K. Sleigh, Phytochemistry, 1978, 17, 899. A. I. Scott, S . L. Lee, P. de Capite, M. G. Culver, and C. R. Hutchinson, Heterocycles, 1977,7,979. C . R. Hutchinson, A. H. Heckendorf, P. E. Daddona, E. Hagaman, and E. Wenkert, J. Amer. Chem. , 1974, 96, 5609; R. B. Herbert, in ref. 6, p. 36; in ref. 7, p. 21. A. H. Heckendorf and C . R. Hutchinson, Tetrahedron Letters, 1977, 4153. J CO,Me Catharanthine (1 12) (113) OMe new detail is that the aglycone (119), derived from the lactam (118),which is a known precursor for ~ a m p t o t h e c i n is , ~not ~ involved in b i o ~ y n t h e s i s .
Alkaloids (v. 9) by Royal Society Of Chemistry