Topic
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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TL;DR: In this article, the authors presented an optically pure α-tert-butyl β-methyl (2S,3R)-3-ethylhexahydroquinolinate (EHQ) in 54-59% yield from L-aspartic acid was the foundation for a practical synthesis of (+)-vincamine.
Abstract: Synthesis of optically pure α-tert-butyl β-methyl (2S,3R)-3-ethylhexahydroquinolinate (18) in 54-59% yield from L-aspartic acid was the foundation for a practical synthesis of (+)-vincamine. This synthesis provides (+)-vincamine, demonstrated to be >99% enantiomerically pure, in 24-26% overall yield from L-aspartic acid
90 citations
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TL;DR: The first enantioselective total synthesis of (-)-calicheamicinone (3), the naturally occurring antipode of the calicheamin aglycon, has been achieved as discussed by the authors.
Abstract: The first enantioselective total synthesis of (-)-calicheamicinone (3), the naturally occurring antipode of the calicheamicin aglycon, has been achieved
90 citations
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TL;DR: The catalyst system PC-Phos/AuNTf2 proved to be specifically efficient to promote the desymmetrization of N-allenamides in excellent yields with satisfactory ee values.
Abstract: Highly enantioselective gold-catalyzed intramolecular cyclization of N-allenamides was implemented by utilizing a designed chiral sulfinamide phosphine ligand (PC-Phos). This represents the first example of highly enantioselective intramolecular cyclization of N-allenamides. The practicality of this reaction was validated in the total synthesis of (R)-desbromoarborescidine A and formal synthesis of (R)-desbromoarborescidine C and (R)-deplancheine. Moreover, the catalyst system PC-Phos/AuNTf2 proved to be specifically efficient to promote the desymmetrization of N-allenamides in excellent yields with satisfactory ee values.
90 citations
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TL;DR: The first total syntheses of taiwaniadducts B, C, and D have been accomplished, and two diterpenoid segments were prepared with high enantiopurity, both through Ir-catalyzed asymmetric polyene cyclization.
Abstract: The first total syntheses of taiwaniadducts B, C, and D have been accomplished. Two diterpenoid segments were prepared with high enantiopurity, both through Ir-catalyzed asymmetric polyene cyclization. A sterically demanding intermolecular Diels–Alder reaction promoted by Er(fod)3 assembled the scaffold of taiwaniadducts B and C. A carbonyl-ene cyclization forged the cage motif of taiwaniadduct D at a late stage, providing over 200 mg of this compound.
90 citations
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TL;DR: The key steps were two ring-expansion reactions, one involving an intramolecular Schmidt reaction and one using a novel variant of the photo-Beckmann rearrangement.
90 citations