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- Title
Total Synthesis of Macaranin B.
- Authors
Matsumoto, Shintaro; Aoyama, Akio; Wakamori, Shinnosuke; Yamada, Hidetoshi
- Abstract
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.
- Subjects
COUPLING reactions (Chemistry); OXIDATIVE coupling; QUINONE compounds
- Publication
Bioscience, Biotechnology & Biochemistry, 2021, Vol 85, Issue 9, p1937
- ISSN
0916-8451
- Publication type
Article
- DOI
10.1093/bbb/zbab120