Abstract
Hedathiosulfonic acids A and B were isolated from the deep-sea urchin Echinocardium cordatum and were determined to be novel 6-undecanethiosulfonic acids by 2D NMR, HRMS, and methylation reaction. The stereostructure of hedathiosulfonic acid A was determined by the analysis of its degradation product, a cyclic β-hydroxysulfone. Hedathiosulfonic acids exhibited acute toxicity. We carried out various model reactions of the olefinic compounds with thiosulfonic acids and proved that, as is the case with natural products, synthesized thiosulfonic acid possessing a carbon-carbon double bond was converted into β-hydroxysulfone in the presence of oxygen.
Original language | English |
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Pages (from-to) | 6405-6412 |
Number of pages | 8 |
Journal | Tetrahedron |
Volume | 58 |
Issue number | 32 |
DOIs | |
Publication status | Published - 2002 Aug 5 |
Externally published | Yes |
Keywords
- Isolation
- Model reaction
- Natural thiosulfonic acid
- Structure determination
ASJC Scopus subject areas
- Biochemistry
- Drug Discovery
- Organic Chemistry