School of Science and Technology, Kwansei Gakuin University, Hyogo, Japan.
Biosci Biotechnol Biochem. 2021 Aug 25;85(9):1937-1944. doi: 10.1093/bbb/zbab120.
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.
本研究描述了马卡瑞宁 B 的全合成，这是一种天然存在的鞣花单宁，含有 1-O-没食子酰基和 3,6-O-马卡酰基，在轴向丰富的 d-葡萄糖中。合成的关键步骤包括使用邻醌单缩酮进行的没食子酰基与 1,2,4-邻乙酰基葡萄糖部分的氧化偶联反应以及氧杂迈克尔加成/消除反应。这有助于构建马卡酰基和马卡瑞宁 B 的首次全合成。
