Tetrahedron Letters

A novel and efficient route to the construction of the 4-oxa-tricyclo [4.3. 1.0] decan-2-one scaffold

NG Li, JX Wang, XR Liu, CJ Lin, QD You, QL Guo

Index: Li, Nian-Guang; Wang, Jin-Xin; Liu, Xiao-Rong; Lin, Chang-Jun; You, Qi-Dong; Guo, Qing-Long Tetrahedron Letters, 2007 , vol. 48, # 37 p. 6586 - 6589

Full Text: HTML

Citation Number: 28

Abstract

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 biomimetic tandem Claisen/Diels–Alder reaction occurred to produce the desired tricyclic scaffold 11a as a single isomer. A rationalization of the excellent region ...