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[reaction: see text] The protected precursor 30 to dolabriferol was generated by a DBU-induced, ester-forming, retro-Claisen process. The required linear carbon chain present in 22 was synthesized by a stereoselective lithium aldol reaction. The necessary aldehyde and ketone fragments were synthesized using stereocontrolled aldol reactions with the ethyl (S)-lactate derived ketone 13.
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http://dx.doi.org/10.1021/ol060347s | DOI Listing |
ACS Cent Sci
November 2024
Department of Chemistry, University of California, Berkeley, California 94720, United States.
Inorg Chem
August 2022
Department of Chemistry and Physics, Louisiana Tech University, 1 Adams Blvd., Ruston, Louisiana 71272, United States.
Volatile lanthanide coordination complexes are critical to the generation of new optical and magnetic materials. One of the most common precursors for preparing volatile lanthanide complexes is the hydrate with the general formula Ln(hfac)(HO) ( = 3 for La-Nd, = 2 for Sm) (hfac = 1,1,1,5,5,5-hexafluoroacetylacetonato). We have investigated the synthesis of Ln(hfac)(HO) using more environmentally sustainable mechanochemical approaches.
View Article and Find Full Text PDFOrg Biomol Chem
October 2019
AVIDIN Ltd., Alsó kikötő sor 11/D, Szeged, H-6726, Hungary.
An IBX/NIS-induced intramolecular oxidative annulation of Mannich-type substrates is reported. This metal-free approach involving iodination, NH-oxidation, intramolecular C-N bond formation, and retro-Claisen-Schmidt sequence provides the construction of imidazo[1,2-a]pyridine, imidazo[1,2-a]pyrimidine as well as imidazo[1,2-a]pyrazine frameworks with yields up to 93%. In addition, a sequential one-pot process is also presented.
View Article and Find Full Text PDFJ Org Chem
May 2019
Institute of Natural Sciences and Mathematics , Ural Federal University, 620000 Ekaterinburg , Russian Federation.
J Am Chem Soc
May 2019
Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering , California Institute of Technology, Pasadena , California 91125 , United States.
In the course of a total synthesis effort directed toward the natural product curcusone C, the Stoltz group discovered an unexpected thermal rearrangement of a divinylcyclopropane to the product of a formal Cope/1,3-sigmatropic shift sequence. Since the involvement of a thermally forbidden 1,3-shift seemed unlikely, theoretical studies involving two approaches, the "trial-and-error" testing of various conceivable mechanisms (Houk group) and an "automatic" approach using the Maeda-Morokuma AFIR method (Morokuma group) were applied to explore the mechanism. Eventually, both approaches converged on a cascade mechanism shown to have some partial literature precedent: Cope rearrangement/1,5-sigmatropic silyl shift/Claisen rearrangement/retro-Claisen rearrangement/1,5-sigmatropic silyl shift, comprising a quintet of five sequential thermally allowed pericyclic rearrangements.
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