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

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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.

LanguageEnglish (US)
Pages3378-3387
Number of pages10
JournalJournal of the American Chemical Society
Volume109
Issue number11
StatePublished - 1987
Externally publishedYes

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Carbolines
Urochordata
Cyclization
Dehydrogenation
Antiviral Agents
Bromides
eudistomin D
eudistomin H
tryptoline
eudistomin E
eudistomin C

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Rinehart, K. L., Kobayashi, J., Harbour, G. C., Gilmore, J., Mascal, M., Holt, T. G., ... 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.

Eudistomins A-Q, β-carbolines from the antiviral Caribbean tunicate Eudistoma olivaceum. / Rinehart, Kenneth L.; Kobayashi, Jun'ichi; Harbour, Gary C.; Gilmore, Jeremy; Mascal, Mark; Holt, Tom G.; Shield, Lois S.; Lafargue, Françoise.

In: Journal of the American Chemical Society, Vol. 109, No. 11, 1987, p. 3378-3387.

Research output: Contribution to journalArticle

Rinehart, KL, Kobayashi, J, Harbour, GC, Gilmore, J, Mascal, M, Holt, TG, Shield, LS & Lafargue, F 1987, 'Eudistomins A-Q, β-carbolines from the antiviral Caribbean tunicate Eudistoma olivaceum' Journal of the American Chemical Society, vol. 109, no. 11, pp. 3378-3387.
Rinehart KL, Kobayashi J, Harbour GC, Gilmore J, Mascal M, Holt TG et al. Eudistomins A-Q, β-carbolines from the antiviral Caribbean tunicate Eudistoma olivaceum. Journal of the American Chemical Society. 1987;109(11):3378-3387.
Rinehart, Kenneth L. ; Kobayashi, Jun'ichi ; Harbour, Gary C. ; Gilmore, Jeremy ; Mascal, Mark ; Holt, Tom G. ; Shield, Lois S. ; Lafargue, Françoise. / Eudistomins A-Q, β-carbolines from the antiviral Caribbean tunicate Eudistoma olivaceum. In: Journal of the American Chemical Society. 1987 ; Vol. 109, No. 11. pp. 3378-3387.
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