A novel and efficient route to the construction of the 4-oxa-tricyclo[4.3.1.0]decan-2-one scaffold

作者：Li Nian Guang; Wang Jin Xin; Liu Xiao Rong; Lin Chang Jun; You Qi Dong^*; Guo Qing Long

来源：Tetrahedron Letters, 2007, 48(37): 6586-6589.

DOI：10.1016/j.tetlet.2007.07.005

• xanthone
• tandem Claisen/Diels-Alder reaction
• 4-oxatricyclo[4.3.1.0]decan-2-one scaffold

A short and efficient route to the synthesis of 4-oxa-tricyclo[4.3.1.0]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 biommetic 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.

• 出版日期2007-9-10
• 单位中国药科大学