Batzellines-isobatzellines

A family of alkaloids characterized by a pyrroloquinone skeleton has been isolated in recent years from several sponges. Included in this family are the batzellines, isobatzellines, damirones, makaluvamines, discorhabdins, prianosins and wayakin. These alkaloids have shown a... [Pg.707]

The sulfide marine metabolites having a pyrroloquinoline skeleton can be divided into three groups the batzellines-isobatzellines, the prianosins-discorhabdins, and the makaluvamines. All of these types of compounds have been isolated from sponges. [Pg.822]

The pyrroloquinone imine 122 is considered to be a key branching point for the biogenesis of damirones, batzellines, isobatzellines, makaluvamines [110], and... [Pg.606]

Like the prianosins and the discorhabdins, the batzellines and isobatzellines are sulfides with a pyrroloquinone skeleton [22]. A deepwater Batzella sponge contained the alkaloids, batzellines A (457) and B (458), which possess methyl sulfide groups. The structure of... [Pg.685]

Yamamura et al. developed an efficient route to the synthesis of the A, B, C, D, and E rings of the prianosins and discorhabdins, which led them successfully to synthesize discorhabdin C (Scheme 59) (210-212). Because their route involves the synthesis of the pyrroloquinoline skeleton of the pyrroloquinoline type alkaloids (213-217), they have also achieved the synthesis of batzelline C and isobatzelline C (213,214). Their synthesis involved first the construction of the C, D, and E rings as in 505, starting from 502, which was synthesized in three steps (212). Reaction of 502 with... [Pg.204]

Chang LC, Otero-Quintero S, Hooper JNA, Bewley CA (2002) Batzelline D and isobatzelline E from the Indopacific sponge Zyzzya fuliginosa. J Nat Prod 65 776-778... [Pg.158]

Roberts D, Joule JA, Bros MA, Alvarez M (1997) Synthesis of pyrrolo[4,3,2-iie]quinolmes from 6,7-dimethoxy-4-methylquinoline. Formal total syntheses of damirones A and B, batzelline C, isobatzelline C, discorhabdin C, and makaluvamines A-D. J Org (Them 62 ... [Pg.160]

Tao XL, Nishiyama S, Yamamura S (1991) Total syntheses of batzelline C and isobatzelline... [Pg.161]

Tao XL, Cheng JF, Nishiyama S, Yamamura S (1994) Synthetic studies on tetrahydropyr-roloquinoline-containing natural products syntheses of discorhabdin C, batzelline C and isobatzelline C. Tetrahedron 50 2017-2028... [Pg.161]

The makaluvamines are a series of about 20 closely related derivatives that are similar to batzelline D and isobatzelline E. The generic term makaluvamine derives from Maka-luva Island in the Fiji Archipelago, where these sponges of the genus Zyzzya were collected (Radisky et al, 1993)... [Pg.1101]

Yamada, F., Hamabuchi, S., Shimizu, A., and Somei, M. (1995) Simple total synthesis of marine alkaloids batzelline C, isobatzelline C, damirone A, and makahivamine A. Heterocycles, 41,1905—1908. [Pg.1284]

Roberts, D., Alvarez, M., and Joule, J.A. (1996) Synthesis of 6-chloro-l,3,4,5-tetrahydro-7,8-dimelhoxy-l-melhylpyrrolo[4,3,2-(fe]quinoline from a quinoline formal total synthesis of batzelline C, isobatzelline C, discorhabdin C and makahivamine D. Tetrahedron Lett., 37,1509-1512. [Pg.1284]

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