| Identification | Back Directory | [Name]
thiarubrine A | [CAS]
63543-09-9 | [Synonyms]
thiarubrine A
1,2-Dithiin, 3-(5-hexene-1,3-diyn-1-yl)-6-(1-propyn-1-yl)- | [Molecular Formula]
C13H8S2 | [MOL File]
63543-09-9.mol | [Molecular Weight]
228.33 |
| Hazard Information | Back Directory | [Description]
Thiarubrine A [3-(5-hexene-1,3-diynyl)-6-(1-propynyl)-1,2-dithiin], a major leaf phytochemical of these trees, has been shown to exhibit a wide spectrum of potent antiviral, antifungal, and antibacterial activities.[1] | [Definition]
ChEBI: Thiarubrine A is an organosulfur heterocyclic compound. | [Biological Activity]
Thiarubrine A is reported to be as effective as fungizone at a concentration of 1 ppm against Candida albicans. The important biological activities and unique structures of 1,2- dithiins have drawn considerable interest among syntheticg and theoretical chemists in recent years.
| [Synthesis]
The above-mentioned 11-step synthesis from 2,4-hexadiyne1,6-diol (9) constitutes the first total synthesis of this highly intriguing antiaromatic natural product thiarubrine A. The novel use of 2-(trimethylsilyl)ethanethiol as the protected sulfur atom for the eventual construction of the 1,2-dithiin heterocycle without employment of dissoleing metalliquid ammonia conditions should find wide applications in the synthesis of natural polyacetylene-containing 1,2-dithiin compounds.
 | [References]
[1] MASATO KOREEDA Wu Y. Chemistry of 1,2-Dithiins. Synthesis of the Potent Antibiotic Thiarubrine A[J]. Journal of the American Chemical Society, 1994, 116 23: 10793-10794. DOI:10.1021/ja00102a058. |
|
|