Postulated biogenesis of WS9885B and progress toward an enantioselective synthesis

Organic Letters

Volumn 1, Issue 4, 1999, Pages 645-648

  Vanderwal, Christopher D ^a   Vosburg, David A ^a   Weiler, Sven ^a   Sorensen, Erik J ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC ANTIBIOTIC; FUSED HETEROCYCLIC RINGS; PALLADIUM; WS 9885B;

ARTICLE; CATALYSIS; CHEMISTRY; CYCLIZATION; STEREOISOMERISM; STREPTOMYCES; SYNTHESIS;

ANTIBIOTICS, ANTINEOPLASTIC; CATALYSIS; CYCLIZATION; HETEROCYCLIC COMPOUNDS WITH 4 OR MORE RINGS; PALLADIUM; STEREOISOMERISM; STREPTOMYCES;

EID: 0033606872     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol990723r     Document Type: Article

References (41)

1. Muramatsu, H.; Miyauchi, M.; Sato, B.; Yoshimura, S. 40th Symposium on The Chemistry of Natural Products, Fukuoka, Japan, 1998, Paper 83, p 487.
2. Rowinsky, E. K.; Donehower, R. C. New Engl. J. Med. 1995, 332, 1004.
3. (a) Schiff, P. B.; Fant, J.; Horwitz, S. B. Nature 1979, 277, 665.
4. (b) Schiff, P. B.; Horwitz, S. B. Proc. Natl. Acad. Sci. U.S.A. 1980, 77, 1561.
5. (a) Roush, W. R.; Gillis, H. R.; Ko, A. I. J. Am. Chem. Soc. 1982, 104, 2269.
6. (b) Marshall, J. A.; Audia, J. E.; Grote, J.; Shearer, B. G. Tetrahedron 1986, 42, 2893.
7. (c) Roush, W. R.; Essenfeld, A. P.; Warmus, J. S. Tetrahedron Lett. 1987, 28, 2447.
8. (d) Roush, W. R. In Advances in Cycloaddition; JAI Press: Greenwich, CT, 1990; Vol. 2, p 91.
9. For reviews of the Knoevenagel reaction, see: (a) Jones, G. Org. React. (N.Y.) 1967, 15, 204.
10. (b) Tietze, L. F.; Beifuss, U. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 2, p 341.
11. For an excellent review of inverse electron demand and hetero Diels-Alder reactions, see: Boger, D. L. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 5, p 451.
12. The concept of performing tandem Knoevenagel-hetero Diels-Alder reactions derives strong precedent from the substantial studies of Tietze and co-workers. For reviews, see: (a) Tietze, L. F. J. Heterocycl. Chem. 1990, 27, 47.
13. (b) Tietze, L. F. Chem. Rev. 1996, 96, 115.
14. Xu, D.; Park, C. Y.; Sharpless, K. B. Tetrahedron Lett. 1994, 35, 2495.
15. Zhong, Y.-L.; Shing, T. K. M. J. Org. Chem. 1997, 62, 2622.
16. Vosburg, D. A.; Weiler, S.; Sorensen, E. J. Angew. Chem., Int. Ed. 1999, 38, 971.
17. (a) Corey, E. J.; Dittami, J. P. J. Am. Chem. Soc. 1985, 107, 256.
18. (b) Corey, E. J.; Lee, J.; Roberts, B. E. Tetrahedron Lett. 1997, 38, 8915.
19. (c) Corey, E. J.; Roberts, B. E. Tetrahedron Lett. 1997, 38, 8919.
20. (a) Sato, M.; Sunami, S.; Sugita, Y.; Kaneko, C. Heterocycles 1995, 41, 1435.
21. (b) Sato, M.; Sugita, Y.; Abiko, Y.; Kaneko, C. Tetrahedron: Asymmetry 1992, 3, 1157.
22. (a) Evans, D. A.; Bartroli, J.; Shih, T. L. J. Am. Chem. Soc. 1981, 103, 2127.
23. (b) Evans, D. A.; Nelson, J. V.; Vogel, E.; Taber, T. R. J. Am. Chem. Soc. 1981, 103, 3099.
24. (c) Evans, D. A.; Nelson, J. V.; Taber, T. R. Top. Stereochem. 1982, 13, 1.
25. (d) Evans, D. A. Aldrichimica Acta 1982, 15, 23.
26. Gage, J. R.; Evans, D. A. Organic Syntheses; Wiley: New York, 1993; Collect. Vol. VIII, p 339.
27. (a) Brandänge, S.; Leijonmarck, H. Tetrahedron Lett. 1992, 33, 3025.
28. (b) Leijonmarck, H. K. E. Chem. Commun. (Stockholm) 1992, 3, 1.
29. The potassium counterion is important, as lithium and sodium acetate enolates reportedly give 11-membered rings resulting from competitive attack on the oxazolidinone carbonyl; see ref 15.
30. In the base-induced Claisen-like cyclization of 9, β-elimination of the C16 acetate group was not observed. Presumably, transition state 1,3-allylic strain discourages deprotonation at C17 (see: Evans, D. A.; Kaldor, S. W.; Jones, T. K.; Clardy, J.; Stout, T. J. J. Am. Chem. Soc. 1990, 112, 7001).
31. (a) Anderson, C. D.; Goodman, L.; Baker, B. R. J. Am. Chem. Soc. 1958, 80, 5247.
32. (b) Ireland, R. E.; Liu, L.; Roper, T. D. Tetrahedron 1997, 53, 13221.
33. (a) Corey, E. J.; Hopkins, P. B. Tetrahedron Lett. 1982, 23, 4871.
34. (b) Trost, B. M.; Caldwell, C. G.; Murayama, E.; Heissler, D. J. Org. Chem. 1983, 48, 3252.
35. 1H NMR analysis at 25 °C revealed a ca. 9:1 ratio of lactol:hydroxy aldehyde tautomers.
36. Müller, S.; Liepold, B.; Roth, G. J.; Bestmann, H. J. Synlett 1996, 521.
37. Boden, C. D. J.; Pattenden, G.; Ye, T. J. Chem. Soc., Perkin Trans. 1 1996, 2417.
38. For reviews of the Stille reaction, see: (a) Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508.
39. (b) Farina, V.; Krishnamurthy, V.; Scott, W. J. Org. React. (N.Y.) 1997, 50, 1.
40. For a review of the Heck reaction, see: de Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379.
41. The reagents and reaction conditions that we employed for this Stille coupling were reported to be effective in the following disclosure (see entry 17 of Table 1): Farina, V.; Kapadia, S.; Krishnan, B.; Wang, C.; Liebeskind, L. S. J. Org. Chem. 1994, 59, 5905.