- Total Synthesis of (R)-Argentilactone and (R)-Goniothalamin Using a Free-Radical Photoredox Approach to α,β-Unsaturated δ-Lactones
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α,β-Unsaturated δ-lactones are structural motifs found in diverse pharmacologically active natural products. In fact, the unsaturated lactone is often responsible for the biological activity. Herein, we report a new approach for the syntheses of (R)-argentilactone and (R)- goniothalamin based on a photoredox intermolecular iodolactonization mediated by a photoredox process. This new approach, already employed in our research group, stands as a new methodology to achieve several natural products containing α,β-Unsaturated δ-lactones.
- Fuentes-Pantoja, Francisco J.,Cordero-Vargas, Alejandro
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supporting information
p. 4433 - 4439
(2021/08/20)
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- DIASTEREOSELECTIVE METHODS FOR SYNTHESIZING COMPOUNDS
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The present invention is directed to novel synthetic methods for preparing a compound of Structural Formula (I): wherein R is —H or a hydroxyl protecting group. Also included are synthetic intermediates described herein.
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Paragraph 0200; 0201
(2015/03/16)
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- A modular approach to aryl-C-ribonucleosides via the allylic substitution and ring-closing metathesis sequence. A stereocontrolled synthesis of all four α-/β- and D-/L-C-nucleoside stereoisomers
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Iridium(I)-catalyzed allylation of the enantiopure monoprotected copper(I) alkoxide, generated from (S)-5a, with the enantiopure allylic carbonates (R)-9a,b has been developed as the key step in a new approach to C-nucleoside analogues. The anomeric cente
- Stambasky, Jan,Kapras, Votech,Stefko, Martin,Kysilka, Ondrej,Hocek, Michal,Malkov, Andrei V.,Kocovsky, Pavel
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experimental part
p. 7781 - 7803
(2011/12/14)
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- Natural feedstocks for diversity-oriented synthesis: Macrolide-like scaffolds from nonactate
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We have been interested in the application of readily available, fermentation-derived natural products as key building blocks for the preparation of natural product-like libraries rich in structural and stereochemical diversity. In this manuscript we describe the conversion of methyl nonactate, derived from nonactin, to a diversable scaffold characteristic of macrolide natural products. The synthesis features a key ring-closing metathesis reaction to form the macrocycle. ARKAT-USA, Inc.
- Sumskaya, Yuliya G.,Swain, P. Whitney,Bergmeier, Stepehen C.,McMills, Mark C.,Priestley, Nigel D.,Wrighta, Dennis L.
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experimental part
p. 144 - 166
(2011/07/07)
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- Ruthenium-catalyzed regio- and enantioselective allylic substitution with water: Direct synthesis of chiral allylic alcohols
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Less is more: A new route to access chiral allylic alcohols through the regio- and enantioselective substitution of monosubstituted allylic chlorides with water has been developed. The reaction is catalyzed effectively by planar-chiral cyclopentadienyl ruthenium complexes (see scheme). Copyright
- Kanbayashi, Naoya,Onitsuka, Kiyotaka
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supporting information; experimental part
p. 5197 - 5199
(2011/06/26)
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- A chemoenzymatic approach to the synthesis of the stereoisomers of a β-adrenergic receptor antagonist
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The four stereoisomers of Δ2-isoxazoline 2, a β-adrenergic receptor antagonist structurally related to Falintolol 1, were prepared by an enzyme-catalyzed kinetic resolution of the unsaturated secondary alcohol (±)-7 followed by its cycloadditio
- Dallanoce, Clelia,De Amici, Marco,Carrea, Giacomo,Secundo, Francesco,Castellano, Sabrina,De Micheli, Carlo
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p. 2741 - 2751
(2007/10/03)
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- Total synthesis of (-)-bulgecinine
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A short synthetic route to (-)-bulgecinine (1), the amino acid moiety of bulgecins, was established by using 1,3-dipolar cycloaddition of N-benzyl- α-methoxycarbonylmethanimine N-oxide (6) to a chiral allylic alcohol (5) with moderate threo selectivity as the key reaction.
- Maeda, Mikiko,Okazaki, Fumiaki,Murayama, Mayumi,Tachibana, Yohko,Aoyagi, Yutaka,Ohta, Akihiro
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p. 962 - 965
(2007/10/03)
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