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

Kenneth L. Rinehart, Jun'ichi Kobayashi, Gary C. Harbour, Jeremy Gilmore, Mark Mascal, Tom G. Holt, Lois S. Shield, Françoise Lafargue

Research output: Contribution to journalArticle

230 Scopus citations

Abstract

Seventeen eudistomins have been isolated from the Caribbean colonial tunicate Eudistoma olivaceum. Twelve are β-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-β-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 β-carbolines, followed by appropriate cyclization, reduction, and dehydrogenation.

Original languageEnglish (US)
Pages (from-to)3378-3387
Number of pages10
JournalJournal of the American Chemical Society
Volume109
Issue number11
StatePublished - 1987
Externally publishedYes

ASJC Scopus subject areas

  • Chemistry(all)

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    Rinehart, K. L., Kobayashi, J., Harbour, G. C., Gilmore, J., Mascal, M., Holt, T. G., Shield, L. S., & Lafargue, F. (1987). Eudistomins A-Q, β-carbolines from the antiviral Caribbean tunicate Eudistoma olivaceum. Journal of the American Chemical Society, 109(11), 3378-3387.