Spirolactone syntheses through a rhodium-catalyzed intramolecular C-H insertion reaction: Model studies towards the synthesis of syringolides

Tetrahedron Letters

Volumn 50, Issue 47, 2009, Pages 6450-6453

  Navarro Villalobos, Mauricio ^a,b   Wood, John L ^a,c  

^a YALE UNIVERSITY   (United States)

^b Department of Obstetrics Gynecology   (United States)

^c Department of Environmental and Radiological Health Sciences   (United States)

Author keywords

C H insertion; Rhodium(II) stabilized carbine; Spirolactones; Stereospecific; Syringolides

Indexed keywords

ACETIC ACID DERIVATIVE; GLYCOLIPID; RHODIUM; SPIRONOLACTONE; SYRINGOLIDE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CRYSTAL STRUCTURE; HYDROGEN BOND; MOLECULAR DYNAMICS; STEREOSPECIFICITY; SYNTHESIS;

EID: 78649725128     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.08.126     Document Type: Article

References (40)

1. Navarro Villalobos, M. Ph.D. Dissertation, Yale University, 2000.
2. (a) Keen, N. T. Adv. Bot. Res. 1999, 30, 291-328;
3. (b) Strange, R. N. Sci Prog. 1998, 81, 35-68;
4. (c) Heath, M. C. Eur. J. Plant. Pathol. 1998, 104, 117-124;
5. (d) Staskawicz, B. J.; Ausubel, F. M.; Baker, B. J.; Ellis, J. G.; Jones, J. D. G. Science 1995, 268, 661-667;
6. (e) Keen, N. T. In Mechanisms of Plant Defense Responses; Fritig, B., Legrand, M., Eds.; Kluwer Academic: Boston, 1993; pp 3-11;
7. (f) Keen, N. T. Plant Mol. Biol. 1992, 19, 109-122;
8. (g) Keen, N. T. Annu. Rev. Genet. 1990, 24, 447-463;
9. (h) Lamb, C. J.; Lawton, M. A.; Dron, M.; Dixon, R. A. Cell 1989, 56, 215-224;
10. (i) Gianinazzi, S. In Plant-Microbe Interactions; Kosuge, T., Nester, E. W., Eds.; Macmillan: New York, 1984; Vol. 1, Chapter 13.
11. (a) Smith, M. J.; Mazzola, E. P.; Sims, J. J.; Midland, S. L.; Keen, N. T.; Burton, V.; Stayton, M. M. Tetrahedron Lett. 1993, 34, 223-226;
12. (b) Midland, S. L.; Keen, N. T.; Sims, J. J.; Midland, M. M.; Stayton, M. M.; Burton, V.; Smith, M. J.; Mazzola, E. P.; Graham, K. J.; Clardy, J. J. Org. Chem. 1993, 58, 2940-2945.
13. Wood, J. L.; Jeong, S.; Salcedo, A.; Jenkins, J. J. Org. Chem. 1995, 60, 286-287.
14. (a) Kuwahara, S.; Moriguchi, M.; Miyagawa, K.; Konno, M.; Kodama, O. Tetrahedron Lett. 1995, 36, 3201-3202;
15. (b) Kuwahara, S.; Moriguchi, M.; Miyagawa, K.; Konno, M.; Kodama, O. Tetrahedron 1995, 51, 8809-8814;
16. (c) Ishihara, I.; Sugimoto, T.; Murai, A. Synlett 1996, 335-336;
17. (d) Ishihara, I.; Sugimoto, T.; Murai, A. Tetrahedron 1997, 53, 16029-16040;
18. (e) Henschke, J. P.; Rickards, R. W. Tetrahedron Lett. 1996, 37, 3557-3560;
19. (f) Henschke, J.; Rickards, R. W. Labelled Cpd. Radiopharm. 1998, 41, 211-220;
20. (g) Honda, T.; Mizutani, H.; Kanai, K. J. Org. Chem. 1996, 61, 9374-9378;
21. (h) Zeng, C.-M.; Midland, S. L.; Keen, N. T.; Sims, J. J. J. Org. Chem. 1997, 62, 4780-4784;
22. (i) Yu, P.; Wang, Q.-G.; Mak, T. C. W.; Wong, H. N. C. Tetrahedron 1998, 54, 1783-1788;
23. (j) Wong, H. N. C. Chin. J. Chem. 2005, 23, 1106-1108;
24. (k) Chênevert, R.; Dasser, M. Can. J. Chem. 2000, 78, 275-279;
25. (l) Chenevert, R.; Dasser, M. J. Org. Chem. 2000, 65, 4529-4531;
26. (m) Varvogli, A.-A. C.; Karagiannis, I. N.; Koumbis, A. E. Tetrahedron 2009, 65, 1048-1058.
27. (a) Yoda, H.; Kawauchi, M.; Takabe, K.; Hosoya, K. Heterocycles 1997, 45, 1895-1898;
28. (b) Di Florio, R.; Rizzacasa, M. A. Aust.J. Chem. 2000, 53, 327-331.
29. Navarro Villalobos, M.; Wood, J. L.; Jeong, S.; Benson, C. L.; Zeman, Z. L.; McCarty, C.; Weiss, M. M.; Salcedo, A.; Jenkins, J. Tetrahedron 2009, 65, 8091-8098.
30. Doyle, M. P.; Dyatkin, A. B. J. Org. Chem. 1995, 60, 3035-3038.
31. C-H insertion reaction conditions for all diazo compounds: To a suspension of Rh2(OAc)4 (1.2-0.5% equiv) in CH2Cl2 at reflux was added dropwise (over a 10 h period via syringe pump) a solution of the diazo compound in CH2Cl2. Rh2(TFA)4 was also tried with 14 and Rh2(cap)4 with 36.
32. (a) Neises, B.; Steglich, W. Angew. Chem., Int. Ed. Engl. 1978, 7, 522-523;
33. (b) Hassner, A.; Alexanian, V. Tetrahedron Lett. 1978, 19, 4475-4478.
34. Baum,J. S.; Shook, D. A.; Davies, H. M. L.; Smith, H. D. Synth. Commun. 1987, 17, 1709-1716.
35. The atomic coordinates for structures 3 and 15-18 have been deposited with the Cambridge Crystallographic Data Centre: Navarro Villalobos, Mauricio. Thesis1 deposition to the Cambridge Structural Database; (a) 3, deposition number CCDC 150205; (b) 15, CCDC 150207; (c) 1 16, CCDC 150206; (d) 17, CCDC 150209; (e) 18, CCDC 150208.
36. (a) Padwa, A.; Kulkarni, Y. S.; Zhang, Z. J. Org. Chem. 1990, 55, 4144-4153;
37. (b) Pelliciari, R.; Natalini, B.; Sadeghpour, B. M.; Marinozzi, M.; Snyder, J. P.; Williamson, B. L.; Kuethe, J. T.; Padwa, A. J. Am. Chem. Soc. 1996, 118, 1-12.
38. Box, V. G. S.; Marinovic, N.; Yiannikouros, G. P. Heterocycles 1991, 32, 245-251.
39. Nudelman, A.; Kelner, R.; Broida, N.; Gottlieb, H. E. Synthesis 1989, 387-388.
40. Taber, D. F.; Ruckle, R. E.,Jr.; Hennessy, M.J.J. Org. Chem. 1986, 51, 4077-4078. Caution: These authors mention MsN3 is potentially explosive. For safety reasons most diazo transfers were performed using p-ABSA.11.