Latonduines A and B, new alkaloids isolated from the marine sponge Stylissa carteri: structure elucidation, synthesis, and biogenetic implications

Roger G Linington; David E Williams; Akbar Tahir; Rob van Soest; Raymond J Andersen

doi:10.1021/ol034950b

Latonduines A and B, new alkaloids isolated from the marine sponge Stylissa carteri: structure elucidation, synthesis, and biogenetic implications

Org Lett. 2003 Jul 24;5(15):2735-8. doi: 10.1021/ol034950b.

Authors

Roger G Linington¹, David E Williams, Akbar Tahir, Rob van Soest, Raymond J Andersen

Affiliation

¹ Department of Chemistry, University of British Columbia, Vancouver, B.C., Canada V6T 1Z1.

PMID: 12868902
DOI: 10.1021/ol034950b

Abstract

[structure: see text] Latonduines A (6) and B (7), two new alkaloids with unprecedented heterocyclic skeletons, have been isolated from the Indonesian marine sponge Stylissa carteri. The structures of the latonduines were elucidated by analysis of spectroscopic data and confirmed by the total synthesis of latonduine A (6). It is proposed that ornithine is the biogenetic precursor to the aminopyrimidine fragment of the latonduines.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkaloids / chemical synthesis
Alkaloids / chemistry*
Alkaloids / isolation & purification
Animals
Heterocyclic Compounds, 3-Ring / chemical synthesis
Heterocyclic Compounds, 3-Ring / chemistry*
Heterocyclic Compounds, 3-Ring / isolation & purification
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
Ornithine / chemistry
Porifera / chemistry*
Pyrimidines / chemistry
Spectrometry, Mass, Electrospray Ionization

Substances

Alkaloids
Heterocyclic Compounds, 3-Ring
Pyrimidines
latonduine A
latonduine B
Ornithine