Total Synthesis of Macaranin B.

This study describes the total synthesis of macaranin B, a naturally occurring ellagitannin containing 1- O -galloyl and 3,6- O -macaranoyl groups in an axial-rich d -glucose. The key steps of the synthesis include an oxidative coupling reaction of galloyl groups with 1,2,4-orthoacetylglucose moiety and oxa -Michael addition/elimination using an orthoquinone monoketal. This facilitates the construction of the macaranoyl group and the first total synthesis of macaranin B. [ABSTRACT FROM AUTHOR]