期刊
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
卷 2007, 期 30, 页码 5117-5125出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.200700430
关键词
enol lactones; reduction; rearrangement; Michael addition; aldol reactions; acylphloroglucinols
The synthesis of bridgehead diprenylated bicyclo[3.3.1]-nonane-2,9-dione, based on a reductive rearrangement of an enol lactone, is presented. The same target could be reached by a one-step sequence involving Michael addition of 2,6-diprenylcyclohexanone onto acrolein and intramolecular aldol reaction. The first method could be extended to the for mation of a compound with gem-dimethyl substituents adjacent to the bridgehead position, but the construction of a suitably substituted enol lactone, with a view to polyprenylated acylphloroglucinol elaboration, could not be achieved. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)
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