期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 73, 期 24, 页码 9576-9583出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo8016814
关键词
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资金
- National Institutes of Health [HL25848]
- Guthikonda Fellowship in Organic Chemistry
- Bristol-Myers Squibb Graduate Fellowship in Synthetic Organic Chemistry
- Sylvia & Victor Fourman Fellowship
Spirotenuipesines A and B, isolated from the entomopathogenic fungus Paecilomyces tenuipes by Oshima and co-workers, have been synthesized. The synthesis features the highly stereoselective construction of two vicinal all-carbon quaternary centers (C-5 and C-6) via an intramolecular cyclopropanation/radical initiated fragmentation sequence and a diastereoselective intermolecular Diels-Alder reaction between alpha-methylenelactone dienophile 20 and synergistic diene 6a. Installation of the C-9 tertiary alcohol occurred via nucleophilic methylation. An RCM reaction to produce a tetrasubstituted double bond in the presence of free allylic alcohol and homoallylic oxygenated functional group is also described. This route shortened the synthesis of 11 from 9 steps to 3 steps. We have further developed a strategy to gain access to optically active spirotenuipesines A and B through the synthesis of enantioenriched 10 from commercially available R-(-)-epichlorohydrin.
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