Alkaloids: Chemistry and Pharmacology, Volume 9 by R.H.F Manske, H.L. Holmes

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By R.H.F Manske, H.L. Holmes

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VII. Synthesis . . . . 78 82 85 85 85 87 91 A. Rerberine and Related Alkaloids tives . . . . . . . . . . . . . 91 . . . . . . 100 . . . . . . . . . . .. . . .. . References . . .. . 102 110 X. Addendum . . . .. . . .. . . . . .. . . . . . . . 110 I. Introduction Since the protoberberine alkaloids were last reviewed in Volume I V of this series, many important developments have taken place in the chemistry of this group of alkaloids.

G'hem. Soc. p. 85 (1964); A. R.. ersby, T. H. Brown, and J. H. Clements, J . Chem. Soc. p. 4550 (1965). 51. A . R . Battcrsby, R . T. Brown, J. H. Clements, and G. G. Iverach, ChewL. Commun. Xo. 11,p. 230 (1965). 51a. A. R. Battersby and T. H. Brown, Chern. Commun. p. I 7 0 (1966). 52. A. H. Jackson ancl J. A. Martin, Chem. Conamun. S o . 8, p. 142 (1965). 53. BI. Shamma and W. A. n. C o m m u n . KO. 21, p. 528 (1965). 54. W. A. Ayer and W. I. Taylor, J . Chem. Soc. p. 452 (1956). 56. T. Kitamura, J .

The chemistry of laurelliptine has been summarized in a very recent paper (22a). E. ROGERSINE The crystalline alkaloid rogersine, C ~ O H ~ ~iCH30H N O ~ . Spectral and analytical data indicated a 1,2,9,10tetrasubstituted aporphine with three methoxyls and one hydroxyl, and by a process of comparison and elimination expression XXXIV was suggested for the alkaloid ( 2 3 ) . A comparative NMR-study then showed that rogersine corresponds to crystalline hr-methyllaurotetanine (XXIX), an alkaloid which had never previously been obtained in a crystalline form.

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