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.
Keywords: axial-rich glucose; ellagitannin; macaranin B; macaranoyl group; total synthesis.
© The Author(s) 2021. Published by Oxford University Press on behalf of Japan Society for Bioscience, Biotechnology, and Agrochemistry.