| 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 |
| lactones |
| 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 https://doi.org/10.1002/chem.202002753. 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) |
| URI: | http://hdl.handle.net/2115/83455 |
| 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)
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