期刊
ORGANIC LETTERS
卷 10, 期 7, 页码 1401-1404出版社
AMER CHEMICAL SOC
DOI: 10.1021/ol800118c
关键词
-
资金
- NIGMS NIH HHS [R01 GM050151, R01 GM050151-16, GM-50151] Funding Source: Medline
Reductive alkylation of methyl 2-methoxybenzoate with prenyl bromide and hydrolysis afforded methyl 6-oxo-1-prenyl-2-cyclohexenecarboxylate. Reduction of the ketone, hydrolysis, iodolactonization, ozonolysis, and intramolecular aldol reaction provided a spiro lactone cyclopentenal. Retro-iodolactonization with activated Zn, formation of the beta-lactone, and reduction of the aldehyde completed an efficient first synthesis of (+/-)-vibralactone. No protecting groups were used except for the novel use of an iodolactone to protect both the prenyl double bond and carboxylic acid.
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