An efficient and stereoselective synthesis of xerulin via Pd-catalyzed cross coupling and lactonization featuring (E)-iodobromoethylene as a novel two-carbon synthon

Organic Letters

Volumn 2, Issue 1, 2000, Pages 65-67

  Negishi, Ei Ichi ^a   Alimardanov, Asaf ^a   Xu, Caiding ^a  

^a PURDUE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

HYPOCHOLESTEROLEMIC AGENT; LACTONE; XERULIN;

ARTICLE; CHEMICAL STRUCTURE; STEREOISOMERISM; SYNTHESIS;

ANTICHOLESTEREMIC AGENTS; LACTONES; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 0033649514     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol990336h     Document Type: Article

References (36)

1. Kuhnt, D.; Anke, T.; Besl, H.; Bross, M.; Herrmann, R.; Mocek, U.; Steffan, B.; Steglich, W. J. Antibiot. 1990, 43, 1413.
2. During the course of our study, the first synthesis of xerulin employing a much different synthetic strategy and lacking stereoselectivity in the critical final step (Wittig olefination) was published [Siegel, K.; Brückner, R. Synlett 1999, 1227]. The same group has also published a total synthesis of dihydroxerulin [Siegel, K.; Brückner, R. Chem. Eur. J. 1998, 3, 1116].
3. During the course of our study, the first synthesis of xerulin employing a much different synthetic strategy and lacking stereoselectivity in the critical final step (Wittig olefination) was published [Siegel, K.; Brückner, R. Synlett 1999, 1227]. The same group has also published a total synthesis of dihydroxerulin [Siegel, K.; Brückner, R. Chem. Eur. J. 1998, 3, 1116].
4. Stolz, R. Chem. Ber. 1886, 19, 536.
5. (a) King, A. O.; Okukado, N.; Negishi, E. J. Chem. Soc., Chem. Commun. 1977, 683.
6. (b) King, A. O.; Negishi, E.; Villani, F. J., Jr.; Silveira, A., Jr. J. Org. Chem. 1978, 43, 1027.
7. (c) Negishi, E. In Aspects of Mechanism and Organometallic Chemistry; Brewster, J. H., Ed.; Plenum Press: New York, 1978; p 287.
8. (d) Negishi, E.; Xu, C.; Tan, Z.; Kotora, M. Heterocycles 1997, 46, 209.
9. (e) Negishi, E.; Kotora, M.; Xu, C. J. Org. Chem. 1997, 62, 8957.
10. Negishi, E.; Okukado, N.; King, A. O.; Van Horn, D. E.; Spiegel, B. J. J. Am. Chem. Soc. 1978, 100, 2254.
11. (a) Negishi, E.; Okukado, N.; Lovich, S. F.; Luo, F. T. J. Org. Chem. 1984, 49, 2629.
12. (b) Kende, A. S.; Smith, C. A. J. Org. Chem. 1988, 53, 2655.
13. (a) Kotora, M.; Negishi, E. Tetrahedron Lett. 1996, 37, 9041.
14. (b) Kotora, M.; Negishi, E. Synthesis 1997, 121.
15. (c) Liu, F.; Negishi, E. J. Org. Chem. 1997, 62, 8591.
16. (d) For a review containing pertinent references, see: Negishi, E.; Kotora, M. Tetrahedron 1997, 53, 6707.
17. For related studies leading to the development of this procedure, see: (a) Lu, X.; Huang, X.; Ma, S. Tetrahedron Lett. 1993, 34, 5963.
18. (b) Kundu, N. G.; Pal, M. J. Chem. Soc., Chem. Commun. 1993, 86.
19. Viehe, H. G.; Franchimont, E. Chem. Ber. 1963, 96, 3153.
20. Bartlome, A.; Stampfli, U.; Neuschwander, M. Chimia 1991, 45, 346.
21. (a) Sonogashira, K.; Tohda, Y.; Hagihara. N. Tetrahedron Lett. 1975, 4467.
22. (b) Dieck, H. A.; Heck, R. F. J. Organomet. Chem. 1975, 93, 259.
23. (a) Zweifel, G.; Polston. N. L. J. Am. Chem. Soc. 1970, 92, 4068.
24. (b) For a review, see: Pelter, A.; Smith, K.; Brown, H. C. Borane Reagents: Academic Press: New York, 1988; p 503.
25. Zweifel, G.; Miller, J. A. Org. React. 1984, 32, 375.
26. (a) For a review, see: Labinger, J. A. In Comprehensive Organic Synthesis: Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 3, pp 667-702.
27. (b) Fryzuk, M. D.; Bates, G. S.; Stone, C. Tetrahedron Lett. 1986, 27, 1537.
28. (c) Crombie, L.; Hobbs, A. J. W.; Horsham, M. A.; Blade, R. J. Tetrahedron Lett. 1987, 28, 4875.
29. (a) Cadiot, P.; Chodkiewicz, W. In Chemistry of Acetylenes: Viehe, H. G., Ed.; Marcel Dekker: New York, 1969; p 597.
30. (b) See, for example: Cai, C.; Vasella, A. Helv. Chim. Acta 1995, 78, 2053.
31. (a) Rotovelomanana, V.; Linstrumelle, G. Tetrahedron Lett. 1981, 22, 315.
32. (b) Alami, M.; Gueugnot, S.; Domingues, E.; Linstrumelle, G. Tetrahedron 1995, 51, 1209.
33. (c) Ramaiandrasoa, P.; Bréhon, B.; Thivet, A.; Alami, M.; Cahiez, G. Tetrahedron Lett. 1997, 38, 2447.
34. (a) Carpita, A.; Rossi, R. Tetrahedron Lett. 1986, 27, 4351.
35. (b) Andreini, B. P.; Benetti, M.; Carpita, A.; Rossi, R. Tetrahedron 1987, 43, 4591.
36. 3) 18.99, 72.55, 79.40, 80.66, 83.36, 109.91, 112.15, 114.69, 118.89, 127.73, 135.07, 135.54, 137.81, 142.53, 143.79, 143.95, 149.46, 169.31.