A Bisphenethylisoquinoline Alkaloid

Melanthioidine (CLXVI) was isolated from Androcymbium melan-thioides Willd. (124) with androcymbine, an alkaloid containing the 1-phenethylisoquinoline system. [Pg.169]

The NlVIR-spectrum was found to be similar to that of 1-phenethyl-isoquinolines. This fact, together with its simplicity and the foregoing information about the functional groups, suggested that the alkaloid has a symmetrical bisphenethylisoquinoline structure. [Pg.169]

The sodium-ammonia cleavage of 0,0-dimethylmelanthioidine (CLXVII) afforded almost exclusively one phenolic compound shown by mass spectrometry and synthesis to have the constitution CLXVIII the configuration was inferred from the ORD-curve of the base. [Pg.169]

The aforementioned results led to the proposal of structure CLXVII for 0,0-dimethylmelanthioidine. The ether linkages were attached to rings C and C as shown on biogenetic grounds. [Pg.170]

Tomita, T. Kikuchi, K. Fujitani, A. Kato, H. Furukawa, Y. Aoyagi, M. Kitano, and T. Ibuka, Tetrahedron Letters p. 857 (1966). [Pg.170]

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