A Very Efficient Route toward the 4a-Methyltetrahydrofluorene Skeleton: Short Synthesis of (±)-Dichroanone and (±)-Taiwaniaquinone H

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• 作者：Enrique Alvarez-Manzaneda ; Rachid Chahboun ; Eduardo Cabrera ; Esteban Alvarez ; Ramn Alvarez-Manzaneda ; Ricardo Meneses ; Hakima Es-Samti ; Antonio Fernndez
• 刊名：Journal of Organic Chemistry
• 出版年：2009
• 出版时间：May 1, 2009
• 年：2009
• 卷：74
• 期：9
• 页码：3384-3388
• 全文大小：206K
• 年卷期：v.74,no.9(May 1, 2009)
• ISSN：1520-6904

文摘

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 α- (11a) or β-cyclocitral (11b).