Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 76, Issue 14, Pages 5515-5523Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo200327d
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Funding
- NIH [CA36622, GM54501590, RR06262, RR14768]
- NSF [DBI-0002806]
- University of Colorado Comprehensive Cancer Center
- UC Denver
- W. M. Keck Foundation
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Four new tris-bromoindole cyclic guanidine alkaloids, araiosamines A-D, were isolated from the methanol extract of a marine sponge, Clathria (Thalysias) araiosa, collected from Vanuatu. Their carbon skeletons delineate a new class of indole alkaloids apparently derived from a linear polymerization process involving a carbon-carbon bond formation. Comparison of the structures including the relative configurations suggests a common intermediate containing a dihydroaminopyrimidine moiety capable of undergoing various modalities of conjugate addition to yield unprecedented ring systems.
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