Stereocontrolled synthesis of the diene and triene macrolactones of oximidines I and II: Organometallic coupling versus standard macrolactonization

Organic Letters

Volumn 3, Issue 22, 2001, Pages 3487-3490

  Coleman, Robert S ^a   Garg, Rahul ^a  

^a OHIO STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; LACTONE; ORGANOMETALLIC COMPOUND; SELENECIC ACID; SELENIUM DERIVATIVE; SELENOL;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; STEREOISOMERISM; SYNTHESIS;

ANTINEOPLASTIC AGENTS; CYCLIZATION; INDICATORS AND REAGENTS; LACTONES; MODELS, MOLECULAR; ORGANOMETALLIC COMPOUNDS; SELENIUM COMPOUNDS; STEREOISOMERISM;

EID: 0035515329     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol016744e     Document Type: Article

References (23)

1. Kim, J. W.; Shin-ya, K.; Furihata, K.; Hayakawa, Y.; Seto, H. J. Org. Chem. 1999, 64, 153-155.
2. Boyd, M. R.; Farina, C.; Belfiore, P.; Gagliardi, S.; Kim, J. W.; Hayakawa, Y.; Beutler, J. A.; McKee, T. C.; Bowman, B. J.; Bowman, E. J. J. Pharmacol. Exp. Ther. 2001, 297, 114-120.
3. For simplified model systems lacking the conjugated diene/triene system, see: Scheufler, F.; Maier, M. E. Synlett 2001, 1221-1224.
4. Wu, Y.; Esser, L.; De Brabander, J. K. Angew. Chem., Int. Ed. 2000, 39, 4308-4310.
5. Snider, B. B.; Song, F. Org. Lett. 2001, 3, 1817-1820.
6. Labrecque, D.; Charron, S.; Rej, R.; Blais, C.; Lamothe, S. Tetrahedron Lett. 2001, 42, 2645-2648.
7. Erickson, K. L.; Beutler, J. A.; Cardellina, J. H.; Boyd, M. R. J. Org. Chem. 1997, 62, 8188-8192.
8. Stephens, R. D.; Castro, C. E. J. Org. Chem. 1963, 28, 2163. Stephens, R. D.; Castro, C. E. J. Org. Chem. 1963, 28, 3313-3315.
9. Stephens, R. D.; Castro, C. E. J. Org. Chem. 1963, 28, 2163. Stephens, R. D.; Castro, C. E. J. Org. Chem. 1963, 28, 3313-3315.
10. 2-sp carbon-carbon bond formation. The Castro-Stephens coupling uses stoichiometric copper, whereas the Sonogashira variant uses catalytic palladium and copper: Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 4467-4470. Sonogashira, K. Cross-Coupling Reactions to sp Carbon Atoms. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. Eds.; Wiley-VCH: New York, 1998; pp 203-229.
11. 2-sp carbon-carbon bond formation. The Castro-Stephens coupling uses stoichiometric copper, whereas the Sonogashira variant uses catalytic palladium and copper: Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 4467-4470. Sonogashira, K. Cross-Coupling Reactions to sp Carbon Atoms. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. Eds.; Wiley-VCH: New York, 1998; pp 203-229.
12. There has been only a single description of the use of either coupling reaction for the synthesis of macrolactones: Yoshimura, F.; Kawata, S.; Hirama, M. Tetrahedron Lett. 1999, 40, 8281-8285.
13. Barry, J.; Bram, G.; Decodts, G.; Loupy, A.; Orange, C.; Petit, A.; Sansoulet, J. Synthesis 1985, 40-45.
14. Hanak, M.; Auchter, G. J. Am. Chem. Soc. 1985, 107, 5238-5245.
15. Takai, K.; Nitta, K.; Utimoto, K. J. Am. Chem. Soc. 1986, 108, 7408-7410.
16. Okuro, K.; Furuune, M.; Enna, M.; Miura, M.; Nomura, M. J. Org. Chem. 1993, 58, 4716-4721.
17. Aerssens, M. H. P. J.; Brandsma, L. J. Chem. Soc., Chem. Commun. 1984, 735-736.
18. Haseltine, J. N.; Cabal, M. P.; Mantlo, N. B.; Iwasawa, N.; Yamashita, D. S.; Coleman, R. S.; Danishefsky, S. J.; Shulte, G. K. J. Am. Chem. Soc. 1991, 113, 3850-3866.
19. Brandes, B. D.; Jacobsen, E. N. J. Org. Chem. 1994, 59, 4378-4380.
20. Pilli, R. A.; de Andrade, C. K. Z.; Souto, C. R. O.; de Meijere, A. J. Org. Chem. 1998, 63, 7811-7819.
21. Jeong, K.; Sjö, P.; Sharpless, K. B. Tetrahedron Lett. 1992, 33, 3833-3836.
22. Mitsunobu, O. Synthesis 1981, 1-28
23. Inanaga, J.; Hirata, K.; Saeki, H.; Katsuki, T.; Yamaguchi, M. Bull. Chem. Soc. Jpn. 1979, 52, 1989-1993.