Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 68, Issue 5, Pages 2014-2017Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo020597w
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Funding
- NCI NIH HHS [5 P30 CA 42014, CA 36622, CA 67786] Funding Source: Medline
- NCRR NIH HHS [1 S10RR 06262] Funding Source: Medline
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Chemical investigation of a Penicillium brocae, obtained from a tissue sample of a Fijian Zyzyya sp. sponge, yielded two known diketopiperazines and three novel cytotoxic polyketides, brocaenols A-C. The brocaenols contain an unusual enolized oxepine lactone ring system that to the best of our knowledge is unprecedented in the literature. The structures were elucidated by using 2D-NMR methods including an INADEQUATE experiment. The absolute stereochemistry of brocaenol A was established by using a modified Mosher method. The taxonomy of the producing fungus was elucidated by using both morphological and rDNA sequence analysis.
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