Domino Strategy for the Stereoselective Construction of Angularly Fused Tricyclic Ethers

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• 作者：B. V. Subba Reddy ; Durgaprasad Medaboina ; S. Gopal Reddy ; V. Hanuman Reddy ; Kiran Kumar Singarapu ; Balasubramanian Sridhar
• 刊名：Journal of Organic Chemistry
• 出版年：2015
• 出版时间：December 18, 2015
• 年：2015
• 卷：80
• 期：24
• 页码：12580-12587
• 全文大小：422K
• ISSN：1520-6904

文摘

A stereoselective synthesis of decahydrofuro[3,2-d]isochromene derivatives has been achieved by the condensation of 2-cyclohexenylbutane-1,4-diol with aldehydes in the presence of a stochiometric amount of BF₃路OEt₂ in dichloromethane at 鈭?8 掳C. Similarly, the condensation of 2-cyclopentenylbutan-1,4-diol with aldehydes provides the corresponding octahydro-2H-cyclopenta[c]furo[2,3-d]pyran derivatives in good yields with high diastereoselectivity. It is an elegant strategy for the quick construction of tricyclic architectures with four contiguous stereogenic centers in a single step. These tricyclic frameworks are the integral part of numerous natural products.