Journal
JOURNAL OF NATURAL PRODUCTS
Volume 85, Issue 8, Pages 2082-2089Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.jnatprod.2c00476
Keywords
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Funding
- JSPS KAKENHI [20H02865]
- Nissan Chemical Corporation Award in Synthetic Organic Chemistry, Japan
- Support for Pioneering Research Initiated by the Next Generation (SPRING)
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Two new bromoditerpenes, azuriaplysins A (1) and B (2), were isolated from the sea hare Aplysia kurodai. Their relative stereostructures were determined by NMR analysis, and their absolute stereostructures were determined through total synthesis. Azuriaplysin B (2) and its enantiomer exhibited moderate cytotoxicity against HeLa S3 cells.
New bromoditerpenes having an alpha-methylene carbonyl structure, azuriaplysins A (1) and B (2), were isolated from the sea hare Aplysia kurodai. Their relative stereostructures were determined based on one-and two-dimensional NMR spectroscopic analysis. In addition, the absolute stereostructures were determined by the total synthesis of both enantiomers of azuriaplysins A (1) and B (2), the key points of which were bromocyclization of farnesol and optical resolution of a key intermediate. Azuriaplysin B (2) and its enantiomer exhibited moderate cytotoxicity against HeLa S3 cells.
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