Longamides

Longamide B (1232) was found in the Caribbean sponge Agelas dispar... 

Patel J, Pelloux-Leon N, Minassian F, Vallee Y (2005) Syntheses of S-Enantiomers of Hanishin, Longamide B, and Longamide B Methyl Ester from L-Cispartic Acid P-Methyl Ester Establishment of Absolute Stereochemistry. J Org Chem 70 9081... 

A novel Pd-catalyzed asymmetric annulation was reported between 5-bromopyrrole-2-carboxylate esters and vinyl aziridines <07OL2357>. The resulting pyrrolopiperazinones such as 58 served as key intermediates in the enantioselective synthesis of longamide B and a number of other pyrrole alkaloids. 

It should be noted that cyclooroidin (38) could be envisaged as the precursor of the nonimidazole bromopyrrole alkaloids longamides (see below). Two cyclooroidin analogs have been isolated agesamide (39) from Agelas sp. [68] and oxocyclostylidol (40) from Stylissa caribica [69]. This latter compound represents the first pyrrole-imidazole alkaloid that includes an oxidized pyrrole moiety. 

New heterocycUc systems usually containing a pyrrole nucleus have been isolated, such as longamide and long-amide B from Agelas longissima and A. dispar, and the manzaddins from Astrosclera willeyana harvested in a submarine cave in the north of the Great Barrier Reef in Australia. 

Patel, J., Pelloux-Leon, N., Minassian, F and Vallee, Y. (2005) Synthesis of S-enantiomers of hanishin, longamide B, and longamide B methyl ester from L-aspartic acid P-methyl ester establishment of absolute stereochemistry. J. Org. Chem.. 70, 9081-9084. 

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