Marine, Nitrogen-containing Heterocyclic Natural Products — Structures and Syntheses of Compounds Containing Indole Units

Abstract

The structures, biological activities, and syntheses of marine natural products containing indole and dihydroindole nuclei are reviewed.The natural product chemistry of sea-dwelling organisms has been developed only over the last twenty years or so;l a fascinating variety of heterocyclic natural products,23 many structurally novel, and many with significant biological acitivity, have been described.Because of the obvious relevance to medicinal chemistry we have reviewed the structures, biological activities, and syntheses of marine alkaloids containing quinoline and/or isoquinoline nuclei?and here deal in the same way with indole-(and dihydroindole-) -containing compounds.5The ancient dye, Tyrian purple (6a121.22 can be obtained from extracts of the hypobronchial glands of numerous mollusks of the genera Murex, Purpura, and Dicathais.The dye is not itself a natural product being produced from a primary precursor, known as tyrindolyl sulphate (7) which has been isolated with, as counterion, choline and choline 3-methylbutenoate from Dicathis orbita and Marcinella beineri respectively,23 or sodium, from Ptychodera flava laysanica.24H Br