Reniera

The synthetic viability of this protocol was demonstrated by the efficient synthesis of an isoindole alkaloid from the Mexican sponge Reniera. a-Cyanosi-lylamine (9) was treated with AgF, in the presence of dipolarophile 10 to furnish the requisite cycloadduct in 68%. An advanced intermediate in the synthesis of nicotine was also prepared by cycloaddition of 11 with phenylvinylsulfone giving the requisite adduct 12 in a 3 1 diastereomic mixture (Schem 3.3). 

Alkylpyridines supposedly lie also along another biosynthetic route, affording pofymeric pyridinium compounds in marine haliclonid sponges the Indo-Pacific Callyspongia fibrosa (Davies-Coleman 1993), the Caribbean Amphimedon compressa (Albrizio 1995), and the Mediterranean Reniera sarai (Sep5i6 1997). 

Guo, Y. Trivelltme, E. Scc amiglio, G. Cimino, G. (1998B) Misenine, a novel macrocyclic alkaloid with an unusual skeleton from the Meditaranean spoa Reniera sp. Tetrahedron, 54, 533-50. 

Sqjcic, K. Guella, G. Mancini, I. Pi ra, F. Dalla Sara, M. Maiestrina, G. Tubbs, K. Macek, P. Turk, T. (1997) Characterization of anticholinesterase-active 3-all lpyridinium polymers frmn the marine sponge Reniera sarai in aqueous solution. J. Nat. Prod., 60, 991-6. 

The Mediterranean sponge Reniera sarai is a rich source of new macro-cyclic alkaloids, named sarains, which may be biogenetically related to petrosin (246) or araguspongins (236-243). The structures of sarains 1-3 (247-249) (2/0) and isosarain 1 (250) (211) were clarified on the basis of extensive spectroscopic analyses. The position of the double bond in 249 remains to be determined. The more polar fraction of this sponge contained three UV-absorbing alkaloids, named sarains A-C. The structure of the diacetylated derivative of sarain A (251) was established by X-ray analyis (2/2). 

Miki, W., Otaki, N., Yokoyama, A., and Kusumi, T., Possible origin of zeaxanthin in the marine sponge Reniera japonica, Experientia, 52, 93, 1996. 

Misenine (78), which possesses an unprecedented tetracyclic cage-like core, was isolated from an unidentified Mediterranean species Reniera sp. [59]. The spatial proximity between the carbonyl and the tertiary amine induces an interaction, or... 

Reniera sarai Pulitzeri-Finali Naples, Italy Bay of Naples 79 [61]... 

Sponges and tunicates contain tetrahydroisoquinoline alkaloids (30). Renieramycin A (105) from a sponge Reniera sp. 

Compounds belonging to this system are less abundant. Only one natural product has been isolated so far from natural resources. The quinone 73 was isolated from the sponge Reniera sp. in 0.001% yield (82JA265). 

Several isoquinolinequinones are natural products. From a bright-blue marine sponge of Reniera sp., renierone (260) was isolated as the major antimicrobial antimetabolite (79TL4163). Later, related quinones were isolated... 

Mancini, Sicurelli, Guella, Turk, MaCek and Sepcic (2004) Fig. (35). Synthesis of oligomeric analogues of poly-APS (77) from Reniera sarai... 

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