An efficient application of the Julia-Kocienski coupling for the olefination of aldehydes with resin-bound benzothiazol-2-yl and 1-phenyl-1H-tetrazol-5-yl sulfones is described. Olefins is generally obtained in high overall yield for the six-reaction steps.
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http://dx.doi.org/10.1007/s11030-010-9251-8 | DOI Listing |
Molecules
August 2024
Shaanxi Key Laboratory for Catalysis, College of Chemical and Environment Science, Shaanxi University of Technology, Hanzhong 723001, China.
The tea tussock moth is a pest that damages tea leaves, affecting the quality and yield of tea and causing huge economic losses. The efficient asymmetric total synthesis of the sex pheromone of the tea tussock moth was achieved using commercially available starting materials with a 25% overall yield in 11 steps. Moreover, the chiral moiety was introduced by Evans' template and the key C-C bond construction was accomplished through Julia-Kocienski olefination coupling.
View Article and Find Full Text PDFOrg Biomol Chem
July 2024
Department of Organic Synthesis and Process Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India.
A practical and efficient synthesis of the C8-C23 fragment of antarlides A-H, incorporating six stereocenters and a conjugated diene, is reported. A strategic combination of synthetic methods, including CBS reduction, Evans' aldol reaction, Keck-Maruoka allylation, and enzymatic resolution, enabled the selective introduction of these stereocenters. Furthermore, the pivotal coupling of key fragments is successfully executed through a Julia-Kocienski olefination reaction, connecting the C8-C14 and C15-C23 subunits.
View Article and Find Full Text PDFOrg Biomol Chem
February 2024
School of Chemical Sciences, Indian Association for the Cultivation of Science, Jadavpur, Kolkata-700032, India.
A convergent strategy for the stereoselective synthesis of the methyl ester of the structurally challenging and highly labile antibacterial polyene polyketide natural product thailandamide A has been developed. The key steps include the Zincke aldehyde reaction, Stille cross coupling, Negishi reaction, Julia-Kocienski olefination, cross metathesis, and the less explored Pd(I)-based Heck coupling to access different unsaturation bonds. Additionally, Urpi acetal aldol, Evans methylation, and Crimmins acetate aldol reactions were employed to construct four out of six asymmetric centers of the molecule.
View Article and Find Full Text PDFJ Org Chem
February 2024
Institute of Organic Chemistry, Gottfried Wilhelm Leibniz Universität Hannover, Schneiderberg 1B, 30167Hannover, Germany.
We are presenting the development of our route for the total synthesis of desepoxy-tedanolide C. Through the obtained analytical data, the proposed structure of tedanolide C is questioned and a different configuration for this natural product is proposed. Key steps of the synthesis are a Kiyooka aldol reaction that builds up the tertiary alcohol flanked by three oxygenated carbon atoms and two aldol reactions used for fragment couplings.
View Article and Find Full Text PDFJ Org Chem
July 2023
Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai 400076, India.
Recently, we synthesized the proposed structure of the fungal glycolipid fusaroside and suggested corrections in its structure with respect to the positions of the double bonds in the lipid portion. Herein, we report the first total synthesis of the proposed revised structure of fusaroside and thereby confirm its structure. The synthesis involved Julia-Kocienski olefination for the construction of fatty acid and its coupling with trehalose at the O4 position followed by late-stage gem-dimethylation as key steps.
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