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Highly Diastereoselective, Tandem, Three-Component Synthesis of Tetrahydrofurans from Ketoaldehydes via Silylated β-Lactone Intermediates

2008; Wiley; Volume: 47; Issue: 27 Linguagem: Inglês

10.1002/anie.200800235

1521-3773

T. Andrew Mitchell, Cunxiang Zhao, Daniel Romo,

Synthetic Organic Chemistry Methods

Angewandte Chemie International EditionVolume 47, Issue 27 p. 5026-5029 Communication Highly Diastereoselective, Tandem, Three-Component Synthesis of Tetrahydrofurans from Ketoaldehydes via Silylated β-Lactone Intermediates† T. Andrew Mitchell Dr., T. Andrew Mitchell Dr. Department of Chemistry, Texas A&M University, P.O. Box 30012, College Station, TX 77842-3012 (USA), Fax: (+1) 979-862-4880 http://www.chem.tamu.edu/rgroup/romoSearch for more papers by this authorCunxiang Zhao Dr., Cunxiang Zhao Dr. Department of Chemistry, Texas A&M University, P.O. Box 30012, College Station, TX 77842-3012 (USA), Fax: (+1) 979-862-4880 http://www.chem.tamu.edu/rgroup/romoSearch for more papers by this authorDaniel Romo Prof., Daniel Romo Prof. [email protected] Department of Chemistry, Texas A&M University, P.O. Box 30012, College Station, TX 77842-3012 (USA), Fax: (+1) 979-862-4880 http://www.chem.tamu.edu/rgroup/romoSearch for more papers by this author T. Andrew Mitchell Dr., T. Andrew Mitchell Dr. Department of Chemistry, Texas A&M University, P.O. Box 30012, College Station, TX 77842-3012 (USA), Fax: (+1) 979-862-4880 http://www.chem.tamu.edu/rgroup/romoSearch for more papers by this authorCunxiang Zhao Dr., Cunxiang Zhao Dr. Department of Chemistry, Texas A&M University, P.O. Box 30012, College Station, TX 77842-3012 (USA), Fax: (+1) 979-862-4880 http://www.chem.tamu.edu/rgroup/romoSearch for more papers by this authorDaniel Romo Prof., Daniel Romo Prof. [email protected] Department of Chemistry, Texas A&M University, P.O. Box 30012, College Station, TX 77842-3012 (USA), Fax: (+1) 979-862-4880 http://www.chem.tamu.edu/rgroup/romoSearch for more papers by this author First published: 16 June 2008 https://doi.org/10.1002/anie.200800235Citations: 23 † We thank the NIH (GM 069784) and the Welch Foundation (A-1280) for funding this work. We thank Kay Morris and Dr. Ziad Moussa, as well as Profs. Dan Singleton and Brian Connell for helpful discussions. Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Graphical Abstract Like falling dominoes! A novel tandem, three-component reaction is described that generates up to two CC bonds, one CO bond, and three additional stereocenters leading to substituted tetrahydrofuran units. This process involves a tandem Mukaiyama aldol-lactonization/reductive cyclization and proceeds via a silylated β-lactone intermediate. The method was applied to prepare the tetrahydrofuran fragment of colopsinol B. Py=2-pyridyl. 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Soc. 1996, 118, 4322. 18A homogeneous solution results after stirring a 1:1 ratio of thiopyridyl ketene acetal and ZnCl2. 1H NMR spectroscopic analysis supports the formation of a tetrahedral complex. See Ref. [15]. Mechanistic studies of the TMAL reaction will be described in a subsequent full paper. 19Although tetrahedral zinc(II) complexes are the most common, several examples of trigonal-bipyramidal zinc(II) are known, see: 19aR. H. Prince in Comprehensive Coordination Chemistry: Zinc and Cadmium, Vol. 5 (Ed.: ), Pergamon, New York, 1987, pp. 925– 1045; 19bR. R. Holmes in Progress in Inorganic Chemistry, Vol. 32 (Ed.: ), Wiley, New York, 1984, pp. 119– 236; 19cW. N. Lipscomb, N. Strater, Chem. Rev. 1996, 96, 2375; 19dC. O. Rodriguez de Barbarin, N. A. Bailey, D. E. Fenton, Q.-Y. He, J. Chem. Soc. Dalton Trans. 1997, 161; 19eW. Oppolzer, R. N. Radinov, Tetrahedron Lett. 1988, 29, 5645. 20For examples of zinc(II) complexes containing a bidentate ligand that forms a four-membered ring with the metal center, see: 20aM. Bonamico, G. Dessy, V. Fares, L. Scaramuzza, J. Chem. Soc. Dalton Trans. 1972, 2515; 20bC. C. Ashworth, N. A. Bailey, M. Johnson, J. A. McCleverty, N. Morrison, B. Tabbiner, J. Chem. Soc. Chem. Commun. 1976, 743; 20cB. Becker, K. Radacki, W. Wojnowski, J. Organomet. Chem. 1996, 521, 39; 20dK. A. Fraser, M. M. Harding, Acta Crystallogr. 1967, 22, 75. 21T. Kubota, M. Tsuda, M. Takahashi, M. Ishibashi, H. Naoki, J. Kobayashi, J. Chem. Soc. Perkin Trans. 1 1999, 3483. To the best of our knowledge, no studies toward the synthesis of this natural product have been reported. Citing Literature Supporting Information Detailed facts of importance to specialist readers are published as ”Supporting Information”. Such documents are peer-reviewed, but not copy-edited or typeset. They are made available as submitted by the authors. Filename Description anie_200800235_sm_miscellaneous_information.pdf1.3 MB miscellaneous information Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article. Volume47, Issue27June 23, 2008Pages 5026-5029 ReferencesRelatedInformation