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Total Synthesis of Mallotusinin

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Title: Total Synthesis of Mallotusinin
Authors: Yamashita, Kohei Browse this author
Kume, Yuji Browse this author
Ashibe, Seiya Browse this author
Puspita, Cicilia A. D. Browse this author
Tanigawa, Kotaro Browse this author
Michihata, Naoki Browse this author
Wakamori, Shinnosuke Browse this author
Ikeuchi, Kazutada Browse this author →KAKEN DB
Yamada, Hidetoshi Browse this author
Keywords: natural products
total synthesis
intramolecular SNAr reactions
Issue Date: 9-Dec-2020
Publisher: Wiley-Blackwell
Journal Title: Chemistry-A European journal
Volume: 26
Issue: 69
Start Page: 16408
End Page: 16421
Publisher DOI: 10.1002/chem.202002753
Abstract: The total synthesis of mallotusinin, which bears a tetrahydroxydibenzofuranoyl (THDBF) bridge between the 2-oxygen and 4-oxygen of glucose on corilagin with a 3,6-O-(R)-hexahydroxydiphenoyl (HHDP) bridge, is described. The key features of the total synthesis are: 1) improvements of our previously reported method to synthesize corilagin; 2) establishment of the THDBF skeleton via an unusual intramolecular SNAr reaction of an HHDP analogue, and 3) the application of a two-step bislactonization strategy for a HHDP bridge construction into the 2,4-O-THDBF bridge. Oxidative phenol coupling of 1,2,4-orthoacetyl-3,6-di-(4-O-benzylgalloyl)-alpha-d-glucopyranose and the orthoester cleavage of the coupling product without the pyranose-furanose ring transformation are key reactions for the improved synthesis of corilagin, which enabled the adequate supply of a corilagin precursor that was required to develop the mallotusinin synthesis. These established methods are expected to help develop the synthesis of other ellagitannins with a bridge between the two oxygens of corilagin.
Rights: This is the peer reviewed version of the following article: Chemistry-A European journal 26(69) December 9, 2020, pp.16408-16421 , which has been published in final form at This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions.
Type: article (author version)
Appears in Collections:理学院・理学研究院 (Graduate School of Science / Faculty of Science) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)

Submitter: 池内 和忠

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