Palladium-Catalyzed DYKAT of Vinyl Epoxides: Enantioselective Total Synthesis and Assignment of the Configuration of (+)-Broussonetine G

Angewandte Chemie - International Edition

Volumn 42, Issue 48, 2003, Pages 5987-5990

  Trost, Barry M ^a   Horne, Daniel B ^a   Woltering, Michael J ^a  

^a STANFORD UNIVERSITY   (United States)

Author keywords

Inhibitors; Natural products; Structure elucidation; Symmetric synthesis; Total synthesis

Indexed keywords

ALKYLATION; CATALYSIS; ENZYMES; NITROGEN COMPOUNDS; SYNTHESIS (CHEMICAL);

ENANTIOSELECTIVITY;

PALLADIUM;

1,2 EPOXY 3 BUTENE; BROUSSONETINE G; EPOXIDE; GLYCOSIDASE INHIBITOR; HETEROCYCLIC COMPOUND; PALLADIUM; PYRROLIDINE DERIVATIVE; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

ALKYLATION; ARTICLE; CATALYSIS; CHEMICAL MODIFICATION; CONFORMATIONAL TRANSITION; ENANTIOSELECTIVITY; SYNTHESIS;

ALKALOIDS; CATALYSIS; ENZYME INHIBITORS; EPOXY COMPOUNDS; PALLADIUM; PYRROLIDINES; STEREOISOMERISM;

EID: 0346724627     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200352857     Document Type: Article

References (22)

1. For reviews on the importance and use of glycosidase inhibitors, see: a) Iminosugars as Glycosidase Inhibitors: Nojirimycin and Beyond (Ed.: A. E. Stutz), Wiley-VCH, Weinheim, 1999;
2. b) N. Asano, R. J. Nash, R. J. Molyneux, G. W. Fleet, Tetrahedron: Asymmetry 2000, 11, 1645.
3. For a recent review of the isolation, biology, and chemistry of broussonetines, see: M. Shibano, D. Tsukamoto, G. Kusano, Heterocycles 2002, 57, 1539.
4. a) R. Saul, J. P. Chambers, R. J. Molyneux, A. D. Elbein, Arch. Biochem. Biophys. 1983, 221, 593;
5. b) R. Saul, J. P. Chambers, R. J. Molyneux, A. D. Elbein, Arch. Biochem. Biophys. 1984, 230, 668;
6. c) B. Winchester, G. W. Fleet, J. Carbohydr. Chem. 2000, 19, 471.
7. M. Shibano, S. Nakamura, N. Akazawa, G. Kusano, Chem. Pharm. Bull. 1998, 46, 1048.
8. H. Yoda, T. Shimojo, K. Takabe, Tetrahedron Lett. 1999, 40, 1335.
9. a) B. M. Trost, Chem. Pharm. Bull. 2002, 50, 1;
10. b) B. M. Trost, D. L. Van Vranken, C. Bingel, J. Am. Chem. Soc. 1992, 114, 9327.
11. For a review on the synthesis and biology of DMDP, see: T. M. Wrodnigg, Monatsh. Chem. 2002, 133, 393.
12. B. M. Trost, R. C. Bunt, R. Lemoine, T. L. Calkins, J. Am. Chem. Soc. 2000, 122, 5968.
13. K. Matsumura, S. Hashiguchi, T. Ikariya, R. Noyori, J. Am. Chem. Soc. 1997, 119, 8738.
14. C. A. Brown, A. Yamashita, J. Am. Chem. Soc. 1975, 97, 891.
15. K. Utimoto, Pure Appl. Chem. 1983, 55, 1845.
16. P. Deslongchamps, Stereoelectronic Effects in Organic Synthesis, Pergamon, Elmsford, NY, 1983.
17. M. Scholl, S. Ding, C. W. Lee, R. H. Grubbs, Org. Lett. 1999, 1, 953.
18. CCDC-218668 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB21EZ, UK; fax: (+44)1223-336-033; or deposit@ ccdc.cam.ac.uk).
19. a) M. M. Midland, Y. C. Kwon, J. Am. Chem. Soc. 1983, 105, 3725.
20. b) S. Ono, S. Shuto, A. Matsuda, Tetrahedron Lett. 1996, 37, 221.
21. B. M. Trost, J. L. Belletire, S. Godleski, P. G. McDougal, J. M. Balkovec, J. J. Baldwin, M. E. Christy, G. S. Ponticello, S. L. Varga, J. P. Springer, J. Org. Chem. 1986, 51, 2370.
22. For an example of diastereoisomeric products with similar NMR spectra, see the synthesis of mosin B: N. Maezaki, N. Kojima, A. Sakamoto, H. Tominaga, C. Iwata, T. Tanaka, M. Monden, B. Damdinsuren, S. Nakamori, Chem. Eur. J. 2003, 9, 389.