期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 74, 期 11, 页码 4104-4109出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo900401k
关键词
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资金
- National Institutes of Health [GM-64831]
Enantioselective syntheses of all of the named chiral members of the cleroindicin family (C-F) are reported. This effort demonstrates the synthetic utility of a 2,4-dihydroxybenzaldehyde as a starting material for natural product synthesis through the use sequential o-quinone methide chemistry and diastereoselective dearomatization. Natural cleroindicin F was shown to be nearly racemic, and an optically pure synthetic sample of cleroindicin F was found to racemize under slightly basic conditions. All other natural chiral cleroindicins are shown to be partially racemic.
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