期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 75, 期 8, 页码 2453-2460出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo1000324
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资金
- NSF [CHE0741968]
- NIH [CA122256]
- NIH/NCI [T32 CA009523]
- National Undersea Research Program at UNCW
- Coral Reef Conservation Program [NOAA NA96RU-0260]
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [0741968] Funding Source: National Science Foundation
Five new steroidal imidazoles, amaranzoles B-F, were isolated from extracts of the marine sponge Phorbas amaranthus along with the known amaranzole A. The C24-N-(4-p-hydroxyphenyl)imidazol-5-yl constitution found in amaranzoles A, C, and D is replaced by a C24-O-(4-p-hydroxyphenyl)imidazole-2-carboxylate motif in amaranzoles B, E, and F. The structures were elucidated by interpretation of spectroscopic data. The C24 side chain configuration was assigned by synthesis of a model ester followed by chiroptical comparisons of its CD spectrum with that of an amaranzole B derivative.
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