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- W3083582304 abstract "A next-generation total synthesis of vancomycin aglycon is detailed that was achieved in 17 steps (longest linear sequence, LLS) from the constituent amino acid subunits with kinetically controlled diastereoselective introduction of all three elements of atropisomerism. In addition to new syntheses of three of the seven amino acid subunits, highlights of the approach include a ligand-controlled atroposelective one-pot Miyaura borylation–Suzuki coupling sequence for introduction of the AB biaryl axis of chirality (>20:1 dr), an essentially instantaneous and scalable macrolactamization of the AB ring system nearly free of competitive epimerization (>30:1 dr), and two room-temperature atroposelective intramolecular SNAr cyclizations for sequential CD (8:1 dr) and DE ring closures (14:1 dr) that benefit from both preorganization by the preformed AB ring system and subtle substituent effects. Combined with a protecting group free two-step enzymatic glycosylation of vancomycin aglycon, this provides a 19-step total synthesis of vancomycin. The approach paves the way for large-scale synthetic preparation of pocket-modified vancomycin analogues that directly address the underlying mechanism of resistance to vancomycin." @default.
- W3083582304 created "2020-09-11" @default.
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- W3083582304 date "2020-09-04" @default.
- W3083582304 modified "2023-10-01" @default.
- W3083582304 title "Next-Generation Total Synthesis of Vancomycin" @default.
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- W3083582304 cites W1985580893 @default.
- W3083582304 cites W1988620336 @default.
- W3083582304 cites W1989797392 @default.
- W3083582304 cites W1990046056 @default.
- W3083582304 cites W1993018802 @default.
- W3083582304 cites W1995179418 @default.
- W3083582304 cites W2002091468 @default.
- W3083582304 cites W2006562967 @default.
- W3083582304 cites W2006594496 @default.
- W3083582304 cites W2008185727 @default.
- W3083582304 cites W2009889907 @default.
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- W3083582304 cites W2017919162 @default.
- W3083582304 cites W2018871698 @default.
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- W3083582304 cites W2026683521 @default.
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- W3083582304 cites W2617790881 @default.
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- W3083582304 cites W2808426925 @default.
- W3083582304 cites W2809495991 @default.
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- W3083582304 doi "https://doi.org/10.1021/jacs.0c07433" @default.
- W3083582304 hasPubMedCentralId "https://www.ncbi.nlm.nih.gov/pmc/articles/7501256" @default.
- W3083582304 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/32885969" @default.
- W3083582304 hasPublicationYear "2020" @default.
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