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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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TL;DR: A new synthesis of cyclopentene-3,5-dione monoacetals is presented as its use in a tandem 1,4-addition-aldol protocol for the catalytic asymmetric total synthesis of (-)-PGE(1) methyl ester represents a new approach to this class of natural products.
Abstract: Catalytic enantioselective 1,4-additions and tandem 1,4-addition−aldol reactions of dialkylzinc reagents to cyclopentene-3,5-dione monoacetals in the presence of an in situ generated Cu(OTf)2/chiral phosphoramidite catalyst result in highly functionalized cyclopentane building blocks with ee's up to 97% A new synthesis of cyclopentene-3,5-dione monoacetals is presented as well as its use in a tandem 1,4-addition−aldol protocol for the catalytic asymmetric total synthesis of (−)-PGE1 methyl ester This synthesis represents a new approach to this class of natural products By using only 3 mol % of an enantiomerically pure catalyst in the key step, the absolute configurations at three stereocenters of the basic structure of the PGE1 are established at once
86 citations
TL;DR: This work reports the first total synthesis of the complex akuammiline alkaloid picrinine, which was first isolated nearly five decades ago, and constitutes a formal synthesis ofThe related polycyclic alkaloids strictamine.
Abstract: We report the first total synthesis of the complex akuammiline alkaloid picrinine, which was first isolated nearly five decades ago. Our synthetic approach features a concise assembly of the [3.3.1]-azabicyclic core, a key Fischer indolization reaction to forge the natural product’s carbon framework, and a series of delicate late-stage transformations to complete the synthesis. Our synthesis of picrinine also constitutes a formal synthesis of the related polycyclic alkaloid strictamine.
86 citations
86 citations
TL;DR: A convergent total synthesis of the ramoplanin A2 and ramoplanose aglycon is disclosed in this paper, where three key subunits composed of residues 3−9 (heptapeptide 15), pentadepsipeptide 26, and pentapeptides 34 (residues 10−14) were sequentially coupled, and cyclized to provide the 49-membered depsipeptides core of the aglycone.
Abstract: A convergent total synthesis of the ramoplanin A2 and ramoplanose aglycon is disclosed. Three key subunits composed of residues 3−9 (heptapeptide 15), pentadepsipeptide 26, and pentapeptide 34 (residues 10−14) were prepared, sequentially coupled, and cyclized to provide the 49-membered depsipeptide core of the aglycon. Key to the preparation of the pentadepsipeptide 26 incorporating the backbone ester was the asymmetric synthesis of an orthogonally protected l-threo-β-hydroxyasparagine and the development of effective and near-racemization free conditions for esterification of its hindered alcohol (EDCI, DMAP, 0 °C). The coupling sites were chosen to maximize the convergency of the synthesis including that of the three subunits, to prevent late stage racemization of carboxylate-activated phenylglycine-derived residues, and to enlist β-sheet preorganization of an acyclic macrocyclization substrate for 49-membered ring closure. As such, macrocyclization at the chosen Phe9-d-Orn10 site may benefit from both ...
86 citations
86 citations