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- W3039006083 abstract "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 S N Ar 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)‐α‐ 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." @default.
- W3039006083 created "2020-07-10" @default.
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- W3039006083 date "2020-11-09" @default.
- W3039006083 modified "2023-10-17" @default.
- W3039006083 title "Total Synthesis of Mallotusinin" @default.
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- W3039006083 doi "https://doi.org/10.1002/chem.202002753" @default.
- W3039006083 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/32614090" @default.
- W3039006083 hasPublicationYear "2020" @default.
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