Total and formal enantioselective synthesis of lyngbic acid and hermitamides A and B

Tetrahedron Letters

Volumn 47, Issue 29, 2006, Pages 5127-5130

  Virolleaud, Marie Alice ^a   Menant, Christine ^a   Fenet, Bernard ^a   Piva, Olivier ^a  

^a UNIVERSITÉ LYON 1   (France)

Author keywords

[No Author keywords available]

Indexed keywords

4 PENTENOIC ACID; ALCOHOL DERIVATIVE; ALKENE DERIVATIVE; AMIDE; BACTERIAL PROTEIN; CAMPHOR; HERMITAMIDE A; HERMITAMIDE B; IMMUNOSUPPRESSIVE AGENT; LYNGBIC ACID; UNCLASSIFIED DRUG;

ARTICLE; ENANTIOSELECTIVITY; LYNGBYA MAJUSCULA; NUCLEAR MAGNETIC RESONANCE; PROTEIN ISOLATION; RING CLOSING METATHESIS; SYNTHESIS;

DRYOBALANOPS; LYNGBYA MAJUSCULA;

EID: 33745044740     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.05.078     Document Type: Article

References (51)

1. Cardellina II J.H., Dalietos D., Marner F.-J., Mynderse J.S., and Moore R.E. Phytochemistry 17 (1978) 2091-2095
2. Mesguiche V., Valls R., Piovetti L., and Peiffer G. Tetrahedron Lett. 40 (1999) 7473-7476
3. Tan L.T., Okino T., and Gerwick W.H. J. Nat. Prod. 63 (2000) 952-955
4. Elayshberg M.E., Blinov K.A., Williams A.J., Martirosian E.R., and Molodtsov S.G. J. Nat. Prod. 65 (2002) 693-703
5. Molodtsov S.G., Elyashberg M.E., Blinov K.A., Williams A.J., Martirosian E.E., Martin G.E., and Lefebvre B. J. Chem. Inf. Comput. Sci. (2004) 1737-1751
6. Kornprobst J.-M. Substances Naturelles d'origine Marine Vol. 1 (2005), Lavoisier Tec & Doc, Paris 167-172
7. Burja A.M., Banaigs B., Abou-Mansour E., Burgess J.G., and Wright P.C. Tetrahedron 57 (2001) 9347-9377
8. Mayer A.M.S., and Gustafson K.R. Int. J. Cancer 105 (2003) 291-299
9. Praud A., Valls R., Piovetti L., and Banaigs B. Tetrahedron Lett. 34 (1993) 5437-5440
10. Nogle L.M., and Gerwick W.H. J. Nat. Prod. 66 (2003) 217-220
11. Fryhle C.B., Williard P.G., and Rybak C.M. Tetrahedron Lett. 33 (1992) 2327-2330
12. Müller C., Voss G., and Gerlach H. Liebigs Ann. Chem. (1995) 673-676
13. Sankaranarayanan S., Sharma A., and Chattopadhyay S. Tetrahedron: Asymmetry 7 (1996) 2639-2643
14. Braddock D.C., and Matsuno A. Synlett (2004) 2521-2524
15. Li Y., Chen J., and Cao X.-P. Synthesis (2006) 320-324
16. Virolleaud M.A., Bressy C., and Piva O. Tetrahedron Lett. 44 (2003) 8081-8084
17. Virolleaud M.A., and Piva O. Synlett (2004) 2087-2090
18. Bressy C., and Piva O. Synlett (2003) 87-90
19. Bressy C., Menant C., and Piva O. Synlett (2005) 577-582
20. Grubbs R.H. Handbook of Metathesis Vols. 1-3 (2003), Wiley-VCH, Weinheim
21. Blechert S., and Connon S.J. Angew. Chem., Int. Ed. 42 (2003) 1900-1923
22. Nicolaou K.C., Bulger P.G., and Sarlah D. Angew. Chem., Int. Ed. 44 (2005) 4490-4527
23. Pfeiffer M.W.B., and Phillips A.J. J. Am. Chem. Soc. 127 (2005) 5334-5335
24. Dewi-Wülfing P., Gebauer J., and Blechert S. Synlett (2006) 487-489
25. Crimmins M.T., and Caussanel F. J. Am. Chem. Soc. 128 (2006) 3128-3129
26. Synthesis of lyngbic acid 1a: To a solution of 4-methoxyundec-1-ene (460 mg, 2.5 mmol) and 4-pentenoic acid 6 (0.051 mL, 0.5 mmol) in dichloromethane (5 mL) was added second generation Grubbs' catalyst (11 mg). The mixture was heated to 40 °C for 7 h. A second portion of Grubbs' catalyst was then added and the mixture was kept warm for 16 h. The solvent was evaporated under reduced pressure and the residue was purified by flash-chromatography on silica (hexanes/AcOEt = 90/10). Acid 1a was obtained as a colorless oil (108 mg, 84%).
27. Alcaide B., and Almendros P. Chem. Eur. J. 9 (2003) 1258-1262
28. Joe D., and Overman L.E. Tetrahedron Lett. 38 (1997) 8635-8638
29. Michalak M., and Wicka J. Synlett (2005) 2277-2280
30. Hong S.-H., Sanders D.P., Lee C.W., and Grubbs R.H. J. Am. Chem. Soc. 127 (2005) 17160-17161
31. Urch C.J. In: Pearson A.J., and Roush W.J. (Eds). Handbook of Reagents for Organic Synthesis (1999), John Wiley, Chichester 418-419
32. El Bialy S.A.A. Med. Chem. Res. 12 (2003) 415-434
33. 4, filtered off, and concentrated under vacuo. After purification by flash-chromatography (hexanes/AcOEt, 50/50), 10 was isolated pure as a beige powder (545 mg, 75%).
34. Hafner A., Duthaler R.O., Marti R., Rihs G., Rothe-Streit P., and Schwarzenbach F. J. Am. Chem. Soc. 114 (1992) 2321-2336
35. Yamamoto Y., and Asao N. Chem. Rev. 93 (1993) 2207-2293
36. Jones P., and Knochel P. J. Org. Chem. 64 (1999) 186-195
37. Loh T.P., Hu Q.Y., Chok Y.K., and Tan K.T. Tetrahedron Lett. 42 (2001) 9277-9280
38. Nokami J., Yoshizane K., Matsuura H., and Sumida S. J. Am. Chem. Soc. 120 (1998) 6609-6610
39. Kurosu M., and Lorca M. Tetrahedron Lett. 43 (2002) 1765-1769
40. Nokami J., Nomiyama K., Shafi S.M., and Kataoka K. Org. Lett. 6 (2004) 1261-1264
41. Lee C.L.K., Lee C.H.A., Tan K.T., and Loh T.P. Org. Lett. 6 (2004) 1281-1283
42. Lee C.H.A., and Loh T.P. Tetrahedron Lett. 45 (2004) 5819-5822
43. Lee C.H.A., and Loh T.P. Tetrahedron Lett. 47 (2006) 809-812
44. Lee C.H.A., and Loh T.P. Tetrahedron Lett. 47 (2006) 1641-1644
45. Capmau M.-L., Chodkiewicz W., Cadiot P., and Fayet A.-M. Bull. Soc. Chem. Fr. (1968) 3233-3234
46. Hamann-Gaudinet B., Namy J.-L., and Kagan H.B. Tetrahedron Lett. 38 (1997) 6585-6588
47. Preparation of (S)-undec-1-en-4-ol 7: To a solution of camphor-derived allylic alcohol (9.6 g, 50 mmol) and camphor sulfonic acid (395 mg, 1.7 mmol) in dichloromethane (17 mL), was added octanal (2.13 g, 16.6 mmol). The solution was stirred at room temperature for 18 h then concentrated under reduced pressure. The residue was purified by flash-chromatography on silica (hexanes/AcOEt, 95/5) to give 7 as a colorless liquid (2.02 g, 72%, 86% ee).
48. Bargiggia, F. Ph.D. Thesis, Université de Lyon I, 2001.
49. Tyrrell E., Tsang M.W.H., Skinner G.A., and Fawcett J. Tetrahedron 52 (1996) 9841-9852
50. To a solution of (S)-undec-1-en-4-ol (60 mg, 0.35 mmol) in dichloromethane (3.5 mL) was added at 0 °C, (S)-2-phenyl propionic acid (58 mg, 0.39 mmol), 4-dimethylaminopyridine (12 mg, 0.1 mmol), and 1,3-dicyclohexylcarbodiimide (80 mg, 0.39 mmol). This solution was stirred 18 h at room temperature, filtered through cotton, and purified on silica. The desired ester was obtained as a colorless oil (103 mg, 97%).
51. 1H NMR spectra of compounds 12: Minor diastereoisomer 12a: δ = 5.71 (m, 0.074H). Major diastereoisomer 12b: δ = 5.53 (m, 0.926H).