Total synthesis and structural reassignment of (+)-dictyosphaeric acid a: A tandem intramolecular michael addition/alkene migration approach

Angewandte Chemie - International Edition

Volumn 49, Issue 32, 2010, Pages 5574-5577

  Burns, Alan R ^a   McAllister, Graeme D ^a   Shanahan, Stephen E ^b   Taylor, Richard J K ^a  

^a UNIVERSITY OF YORK   (United Kingdom)

^b GLAXOSMITHKLINE   (United Kingdom)

Author keywords

Dictyosphaeric acid; Metathesis michael addition; Tandem reactions total synthesis

Indexed keywords

MICHAEL ADDITIONS; NMR STUDIES; RING-CLOSING METATHESIS REACTIONS; SYNTHETIC ROUTES; TANDEM REACTION; TITLE COMPOUNDS; TOTAL SYNTHESIS;

ADDITION REACTIONS; SYNTHESIS (CHEMICAL);

ACIDS;

ALKENE; ANTIINFECTIVE AGENT; DICTYOSPHAERIC ACID A; LACTONE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; GREEN ALGA; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOISOMERISM; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

ALKENES; ANTI-BACTERIAL AGENTS; CHLOROPHYTA; CRYSTALLOGRAPHY, X-RAY; LACTONES; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 77955024983     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201002416     Document Type: Article

References (19)

1. T. S. Bugni, J. E. Janso, R. T. Williamson, X. Feng, V. S. Bernan, M. Greenstein, G. T. Carter, W. M. Maiese, C. M. Ireland, J. Nat. Prod. 2004, 67, 1396.
2. M. Ivancic, V. L. Hsu, Biopolymers 2000, 54, 35.
3. M. Inoue, H. Takenaka, T. Tsurushima, H. Miyagawa, T. Ueno, Tetrahedron Lett. 1996, 37, 5731.
4. C. W. Barfoot, A. R. Burns, M. G. Edwards, M. N. Kenworthy, M. Ahmed, S. E. Shanahan, R. J. K. Taylor, Org. Lett. 2008, 10, 353.
5. M. G. B. Drew, A. Jahans, L. M. Harwood, S. A. B. H. Apoux, Eur. J. Org. Chem. 2002, 3589.
6. J. G. Marrero, L. M. Harwood, Tetrahedron Lett. 2009, 50, 3574.
7. M. T. Barros, C. D. Maycock, M. R. Ventura, J. Chem. Soc. Perkin Trans. 1 2001, 166.
8. D. M. Knapp, E. P. Gillis, M. D. Burke, J. Am. Chem. Soc. 2009, 131, 6961.
9. M. J. Burns, I. J. S. Fairlamb, A. R. Kapdi, R. J. K. Taylor, Org. Lett. 2007, 9, 5397.
10. S-(+)-Hex-5-en-2-ol (99.3% optical purity) is commercially available.
11. M. Wedel, A. Walter, F.-P. Montforts, Eur. J. Org. Chem. 2001, 1681.
12. H. Wissmann, H. J. Kleiner, Angew. Chem. 1980, 92, 129;
13. Angew. Chem. Int. Ed. Engl. 1980, 19, 133.
14. S. B. Garber, J. S. Kingsbury, B. L. Gray, A. H. Hoveyda, J. Am. Chem. Soc. 2000, 122, 8168.
15. CCDC 764933 (17) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre at www.ccdc.cam.ac.uk/data-request/cif.
16. P. Dupau, R. Epple, A. A. Thomas, V. V. Fokin, K. B. Sharpless, Adv. Synth. Catal. 2002, 344, 421.
17. R. J. K. Taylor, M. Reid, J. Foot, S. A. Raw, Acc. Chem. Res. 2005, 38, 851.
18. Y. Ito, T. Hirao, T. Saegusa, J. Org. Chem. 1978, 43, 1011.
19. After the preparation of this manuscript, a pre-print was sent to Professor C. M. Ireland, University of Utah, who replied (email correspondence dated April 21, 2010) stating that "The hydroxy at C6 is up and the stereochemistry R. It would appear that there was an error made in translating the stereoview to a flat drawing."