A novel and efficient route to the construction of the 4-oxa-tricyclo[4.3.1.0]decan-2-one scaffold |
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Authors: | Nian-Guang Li Xiao-Rong Liu Qi-Dong You Qing-Long Guo |
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Institution: | a Department of Medicinal Chemistry, China Pharmaceutical University, 24 Tongjiaxiang, Nanjing 210009, PR China b Department of Physiology, China Pharmaceutical University, 24 Tongjiaxiang, Nanjing 210009, PR China |
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Abstract: | A short and efficient route to the synthesis of 4-oxa-tricyclo4.3.1.0]decan-2-one scaffold 12 in good yield is reported. Essential to the synthesis was the implementation of selective protection of the catechol system in xanthone 2 with Ph2CCl2 and MOM groups. Subsequently, a biomimetic tandem Claisen/Diels-Alder reaction occurred to produce the desired tricyclic scaffold 11a as a single isomer. A rationalization of the excellent region and stereoselectivity of this transformation was also proposed. |
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Keywords: | Xanthone Tandem Claisen/Diels-Alder reaction 4-Oxa-tricyclo[4 3 1 0]decan-2-one scaffold |
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