Enantioselective Total Synthesis and Biological Evaluation of (+)-Kibdelone A and a Tetrahydroxanthone Analogue

详细信息    查看全文

• 作者：Dana K. Winter ; Mary Ann Endoma-Arias ; Tomas Hudlicky ; John A. Beutler ; John A. Porco ; Jr.
• 刊名：The Journal of Organic Chemistry
• 出版年：2013
• 出版时间：August 2, 2013
• 年：2013
• 卷：78
• 期：15
• 页码：7617-7626
• 全文大小：505K
• 年卷期：v.78,no.15(August 2, 2013)
• ISSN：1520-6904

文摘

The total synthesis of kibdelone A has been accomplished via In(III)-catalyzed arylation of a heterocyclic quinone monoketal and iodine-mediated oxidative photochemical electrocyclization for construction of the ABCD ring moiety. Enzymatic dihydroxylation of methyl 2-halobenzoate substrates was employed for synthesis of activated 2-halo-cyclohexene F-ring fragments. A one pot oxa-Michael/Friedel鈥揅rafts process allowed access to the first simplified DEF ring analogues of the kibdelones.