Eudistomins A-Q, .beta.-carbolines from the antiviral Caribbean tunicate Eudistoma olivaceum

• Published in: Journal of the American Chemical Society Vol. 109; no. 11; pp. 3378 - 3387
• Main Authors: Rinehart, Kenneth L, Kobayashi, Junichi, Harbour, Gary C, Gilmore, Jeremy, Mascal, Mark, Holt, Tom G, Shield, Lois S, Lafargue, Francoise
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 01.05.1987; Amer Chemical Soc
• Subjects: Biological and medical sciences; Chemistry; Chemistry, Multidisciplinary; General pharmacology; Medical sciences; Pharmacology. Drug treatments; Physical Sciences; Physicochemical properties. Structure-activity relationships; Science & Technology; Marine environment; Animal origin; Antiviral; Isolation
• ISSN: 0002-7863; 1520-5126
• DOI: 10.1021/ja00245a031

Seventeen eudistomins have been isolated from the Caribbean colonial tunicate Eudistoma olivaceum. Twelve are .beta.-carbolines-four of them (eudistomins D, J, N, and O) unsubstituted at C-1, three (A, B, and M) with pyrrol-2-yl substituents at C-1, and five (G, H, I, P, and Q) with 1-pyrrolin-2-yl substituents at C-1; five (eudistomins C, E, F, K, and L) are 1,2,3,4-tetrahydro-.beta.-carbolines with an oxathiazepine ring fused at C-1 and N-2. Syntheses are described of eudistomins D, H, I, M, N, O, and Q and of two related compounds. The major route to both 1-(pyrrol-2-yl)- and 1-(1-pyrrolin-2-yl)-substituted eudistomins proceeded through Grignard addition of 2-(1,3-dioxa-2-cyclohexyl)ethyl bromide to 1-cyano-substituted .beta.-carbolines, followed by appropriate cyclization, reduction, and dehydrogenation.