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Total synthesis of gonytolides C and G, lachnone C, and formal synthesis of blennolide C and diversonol.
- Source :
-
Organic & biomolecular chemistry [Org Biomol Chem] 2014 Aug 14; Vol. 12 (30), pp. 5601-10. Date of Electronic Publication: 2014 Jun 23. - Publication Year :
- 2014
-
Abstract
- The first stereoselective total synthesis of gonytolide C, which is a monomeric unit of an innate immune promoter gonytolide A, has been accomplished from the aldol reaction between acetophenone derived from orcinol and butyrolactone containing α-keto ester followed by the excellent diastereoselective intramolecular cyclization. The first total synthesis of gonytolide G has been achieved by the oxidation of benzylic methyl in gonytolide C. Additionally, total synthesis of lachnone C and a formal synthesis of blennolide C and diversonol have been achieved by this synthetic method.
- Subjects :
- 4-Butyrolactone chemical synthesis
4-Butyrolactone chemistry
Chromones chemistry
Lactones chemistry
Proton Magnetic Resonance Spectroscopy
Stereoisomerism
Temperature
Time Factors
Xanthones chemistry
4-Butyrolactone analogs & derivatives
Chromones chemical synthesis
Lactones chemical synthesis
Xanthones chemical synthesis
Subjects
Details
- Language :
- English
- ISSN :
- 1477-0539
- Volume :
- 12
- Issue :
- 30
- Database :
- MEDLINE
- Journal :
- Organic & biomolecular chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 24953777
- Full Text :
- https://doi.org/10.1039/c4ob00950a