期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 74, 期 9, 页码 3384-3388出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo900153y
关键词
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资金
- Spanish Ministry of Science and Technology [CTQ2006-12697]
- Junta de Andalucia
A very expedient and efficient new route toward taiwaniaquinoids, bearing the 4a-methyltetrahydrofluorene skeleton, is reported. Key steps are the intramolecular Friedel-Crafts alkylation of an aryldiene and the degradative oxidation of a methylenedioxy group; the latter process could also be utilized for building the 2-hydroxy-1,4-benzoquinone unit, which is frequently found in natural products. Utilizing this new methodology, (+/-)-dichroanone (7) (three steps, 77% overall yield) and (+/-)-taiwaniaquinone H (6) (four steps, 70% overall yield) have been synthesized from commercial alpha- (11a) or beta-cyclocitral (11b).
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