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Total synthesis
About: Total synthesis is a research topic. Over the lifetime, 25578 publications have been published within this topic receiving 489319 citations.
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85 citations
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TL;DR: A number of valuable new synthetic strategies, such as triazene-driven biaryl ether synthesis, have been developed during the total synthesis of vancomycin this article, which was then assembled to the appropriate peptide fragments.
Abstract: A number of valuable new synthetic strategies, such as the triazene-driven biaryl ether synthesis, have been developed during the total synthesis of vancomycin (1). Modern catalytic asymmetric reactions were employed for the construction of the required amino acid building blocks, which were then assembled to the appropriate peptide fragments, whose cyclization in the order C-O-D→AB/C-O-D→AB/C-O-D-E led to framework of the vancomycin aglycon (2). Sequential attachment of the required sugar moieties onto a suitably protected aglycon derivative, followed by deprotection, allowed the stereoselective total synthesis of the glycopeptide antibiotic vancomycin (1).
85 citations
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TL;DR: The synthetic efforts validate the modified biogenetic hypothesis and allow the absolute configuration of bolivianine to be confirmed, allowing the single-step assembly of a tricyclic system with proper configuration.
Abstract: We report the first total synthesis of bolivanine in a 14-step pathway involving the synthesis of onoseriolide. Our synthesis features a palladium-catalyzed intramolecular cyclopropanation involving an allylic metal carbene and a Diels–Alder/intramolecular hetero-Diels–Alder cascade, allowing the single-step assembly of a tricyclic system with proper configuration. The synthetic efforts validate our modified biogenetic hypothesis and allow us to confirm the absolute configuration of bolivianine.
85 citations