Alkaloids (v. 9) by Royal Society Of Chemistry

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Hayakawa, Y. Baba, S. Makjno, and R. Noyori, J. Amer. Chem. , 1978,100, 1786. 2o J. J. Tufariello and G . B. Mullen, J. Amer. Chem. , 1978, 100, 3638; cf. , Tetrahedron Letters, 1978, 1733. *l As a new development, betalamic acid, the major building block of the betalaine pigments, was prepared as its dimethyl ester (19)22from N-benzylnorteloidinone (16) via the major intermediates (17) and (18), as shown in Scheme 1. phCH&yqo ---+ PhCO&-N --* HO (16) 0 II ROHO P h i 0 -NpcHo OH (17) 0 O O OAc (18) m)-Jlk Me0,C - Me0,C (19) Reagents: i, Pb(OAc),, PhH, MeOH Scheme 1 as a starting material for the synthesis of a showTeloidinone was domycin analogue (23), a C-nucleoside, in which the ribofuranosyl ring oxygen was replaced by a N-carbomethoxy-group.

Bagley and Th. N. Riley, J. , 1977, 14, 599. l7 See 'Tropane Alkaloids', in these Reports, Vol. 5, p. 69; Vol. 6, p. 67. l 8 See 'Tropane Alkaloids', in these Reports, Vol. 7, p. 50. Y. Hayakawa, Y. Baba, S. Makjno, and R. Noyori, J. Amer. Chem. , 1978,100, 1786. 2o J. J. Tufariello and G . B. Mullen, J. Amer. Chem. , 1978, 100, 3638; cf. , Tetrahedron Letters, 1978, 1733. *l As a new development, betalamic acid, the major building block of the betalaine pigments, was prepared as its dimethyl ester (19)22from N-benzylnorteloidinone (16) via the major intermediates (17) and (18), as shown in Scheme 1.

Perkin 11, 1977, 1202. ' I J. Feeney, R. Foster, and E. A. Piper, J. C. S. Perkin ZI, 1977, 2016. P. J. Pauling and T. J. Petcher, Chem. , 1969, 1001; Nature, 1970,228,673. l 3 N. Mandava and G. Fodor, Canad. J. , 1968,46,2761. l4 V. I. Stenberg, S. P. Singh, and N. K. Narain, J. Org. , 1977, 42, 2244. l 5 Th. A . Hamor, J. C. S. PerkinZI, 1977, 1359. l 6 J. R. Bagley and Th. N. Riley, J. , 1977, 14, 599. l7 See 'Tropane Alkaloids', in these Reports, Vol. 5, p. 69; Vol. 6, p. 67. l 8 See 'Tropane Alkaloids', in these Reports, Vol.

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