First total synthesis and determination of the absolute configuration of the stress factor (+)-hydroxymyoporone

Chemistry - A European Journal

Volumn 5, Issue 10, 1999, Pages 2885-2889

  Tietze, Lutz F ^a   Wegner, Christoph ^a   Wulff, Christian ^a  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

Author keywords

Allylation; Asymmetric synthesis; Natural products; Sesquiterpenes

Indexed keywords

ALLYL ALCOHOL; HYDROXYMYOPORONE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; ENANTIOMER; FUSARIUM SOLANI; OPTICAL ROTATION; OXIDATION; POTATO; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0032859499     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3765(19991001)5:10<2885::AID-CHEM2885>3.0.CO;2-8     Document Type: Article

References (30)

1. K. Tange, Bull. Chem. Soc. Jpn. 1981, 54, 2763.
2. L. T. Burka, L. Kuhnert, B. J. Wilson, T. M. Harris, Tetrahedron Lett. 1974, 46, 4017.
3. I. Kitagawa, Z. Cui, B. W. Son, M. Kobayashi, Y. Kyogoku, Chem. Pharm. Bull. 1987, 35, 124.
4. M. Kuroyanagi, A. Ueno, K. Ujiie, S. Sato, Chem. Pharm. Bull. 1987, 35, 53.
5. J. Mulzer, Angew. Chem. 1991, 103, 1484; Angew. Chem. Int. Ed. Engl. 1991, 30, 1452.
6. J. Mulzer, Angew. Chem. 1991, 103, 1484; Angew. Chem. Int. Ed. Engl. 1991, 30, 1452.
7. K. B. Sharpless, E. N. Jacobsen in Catalytic Asymmetric Synthesis (Ed.: I. Ojima), VCH, Weinheim, 1993, pp. 101-272.
8. R. Stürmer, K. Ritter, R. W. Hoffmann, Angew. Chem. 1993, 105, 112; Angew. Chem. Int. Ed. Engl. 1993, 32, 101.
9. R. Stürmer, K. Ritter, R. W. Hoffmann, Angew. Chem. 1993, 105, 112; Angew. Chem. Int. Ed. Engl. 1993, 32, 101.
10. L. F. Tietze, C. Wegner, C. Wulff, Eur. J. Org. Chem. 1998, 1639; L. F. Tietze, K. Schiemann, C. Wegner, C. Wulff, Chem. Eur. J. 1998, 4, 1862; L. F. Tietze, C. Wegner, C. Wulff, Synlett 1996, 471; L. F. Tietze, K. Schiemann, C. Wegner, J. Am. Chem. Soc. 1995, 117, 5851.
11. L. F. Tietze, C. Wegner, C. Wulff, Eur. J. Org. Chem. 1998, 1639; L. F. Tietze, K. Schiemann, C. Wegner, C. Wulff, Chem. Eur. J. 1998, 4, 1862; L. F. Tietze, C. Wegner, C. Wulff, Synlett 1996, 471; L. F. Tietze, K. Schiemann, C. Wegner, J. Am. Chem. Soc. 1995, 117, 5851.
12. L. F. Tietze, C. Wegner, C. Wulff, Eur. J. Org. Chem. 1998, 1639; L. F. Tietze, K. Schiemann, C. Wegner, C. Wulff, Chem. Eur. J. 1998, 4, 1862; L. F. Tietze, C. Wegner, C. Wulff, Synlett 1996, 471; L. F. Tietze, K. Schiemann, C. Wegner, J. Am. Chem. Soc. 1995, 117, 5851.
13. L. F. Tietze, C. Wegner, C. Wulff, Eur. J. Org. Chem. 1998, 1639; L. F. Tietze, K. Schiemann, C. Wegner, C. Wulff, Chem. Eur. J. 1998, 4, 1862; L. F. Tietze, C. Wegner, C. Wulff, Synlett 1996, 471; L. F. Tietze, K. Schiemann, C. Wegner, J. Am. Chem. Soc. 1995, 117, 5851.
14. L. T. Burka, L. Kuhnert, B. J. Wilson, T. M. Harris, J. Am. Chem. Soc. 1977, 99, 2302.
15. L. F. Tietze, U. Beifuss, Angew. Chem. 1993, 105, 137; Angew. Chem. Int. Ed. Engl. 1993, 32, 131; L. F. Tietze, Chem. Rev. 1996, 96, 115.
16. L. F. Tietze, U. Beifuss, Angew. Chem. 1993, 105, 137; Angew. Chem. Int. Ed. Engl. 1993, 32, 131; L. F. Tietze, Chem. Rev. 1996, 96, 115.
17. L. F. Tietze, U. Beifuss, Angew. Chem. 1993, 105, 137; Angew. Chem. Int. Ed. Engl. 1993, 32, 131; L. F. Tietze, Chem. Rev. 1996, 96, 115.
18. A similar substance to 11a was prepared by an enantioselective epoxidation and reductive opening of the oxirane ring in seven steps starting from 3-methyl-2-buten-1-ol: V. Bolitt, C. Mioskowski, R. K. Bhatt, J. R. Falck, J. Org. Chem. 1991, 56, 4238.
19. Crystallographic data (excluding structure factors) for the structure reported for compound 11b has been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-133701. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: (+44) 1223-336-033; e-mail: deposit@ccdc.cam.ac.uk).
20. P. Kocienski, S. D. A. Street, C. Yeates, S. F. Campbell, J. Chem. Soc. Perkin Trans. 1 1987, 2171.
21. T. W. Greene, P. G. M. Wuts, Protective Groups in Organic Synthesis, Wiley, New York, 1991; P. Kocienski, Protecting Groups, Thieme, Stuttgart, 1994.
22. T. W. Greene, P. G. M. Wuts, Protective Groups in Organic Synthesis, Wiley, New York, 1991; P. Kocienski, Protecting Groups, Thieme, Stuttgart, 1994.
23. A. K. M. Anisuzzaman, R. L. Winler, Carbohydr. Res. 1978, 61, 511.
24. K. Deuchert, U. Hertenstein, S. Hünig, G. Wehner, Chem. Ber. 1979, 112, 2045.
25. S. V. Ley, J. Norman, W. P. Griffith, S. P. Marsden, Synthesis 1994, 639.
26. D. B. Dess, J. C. Martin, J. Org. Chem. 1983, 48, 4155; R. E. Ireland, L. Liu, J. Org. Chem. 1993, 58, 2899.
27. D. B. Dess, J. C. Martin, J. Org. Chem. 1983, 48, 4155; R. E. Ireland, L. Liu, J. Org. Chem. 1993, 58, 2899.
28. C. Wegner, Dissertation, Cuvillier-Verlag, Göttingen, 1996.
29. F. Bohlmann, C. Zdero, Phytochem. 1978, 17, 1595.
30. E. Dimitriadis, R. A. Massy-Westropp, Phytochem. 1984, 23, 1325.