Investigations of the stereoselectivity of the intramolecular Diels-Alder reaction of a spiculoic acid model system

Tetrahedron

Volumn 64, Issue 21, 2008, Pages 4852-4867

  Crossman, Julia S ^a   Perkins, Michael V ^a  

^a FLINDERS UNIVERSITY   (Australia)

Author keywords

Intramolecular Diels Alder reaction; Spiculoic acids; Substrate controlled aldol reaction

Indexed keywords

ALKADIENE; BORON; KETONE DERIVATIVE; NATURAL PRODUCT; SPICULOIC ACID; TITANIUM; UNCLASSIFIED DRUG;

ALDOL REACTION; ARTICLE; CHEMICAL MODEL; DIELS ALDER REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; MOLECULAR DYNAMICS; PRIORITY JOURNAL; STEREOCHEMISTRY; STRUCTURE ANALYSIS; WITTIG REACTION;

ALNUS;

EID: 42249084560     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.02.109     Document Type: Article

References (42)

1. Huang X.-H., van Soest R., Roberge M., and Andersen R.J. Org. Lett. 6 (2004) 75-78
2. Berrue F., Thomas O.P., Fernandez R., and Amade P. J. Nat. Prod. 68 (2005) 547-549
3. Stocking E.M., and Williams R.M. Angew. Chem., Int. Ed. 42 (2003) 3078-3115
4. Oikawa H., and Tokiwano T. Nat. Prod. Rep. 21 (2004) 321-352
5. Oikawa H. Bull. Chem. Soc. Jpn. 78 (2005) 537-554
6. Oikawa H., Katayama K., Suzuki V., and Ichihara A. J. Chem. Soc., Chem. Commun. (1995) 1321-1322
7. Katayama K., Kobayashi K., Oikawa H., Honma M., and Ichihara A. Biochim. Biophys. Acta 1384 (1998) 387-395
8. Auclair K., Sutherland A., Kennedy J., Witter D.J., Van den Heever J.P., Hutchinson C.R., and Vederas J.C. J. Am. Chem. Soc. 122 (2000) 11519-11520
9. Watanabe K., Mie T., Ichihara A., Oikawa H., and Honma M. J. Biol. Chem. 275 (2000) 38393-38401
10. Oikawa H., Watanabe K., Yagi K., Ohashi S., Mie T., Ichihara A., and Honma M. Tetrahedron Lett. 40 (1999) 6983-6986
11. Watanabe K., Oikawa H., Yagi K., Ohashi S., Mie T., Ichihara A., and Honma M. J. Biochem. (Tokyo) 127 (2000) 467-473
12. Mehta G., and Kunda U.K. Org. Lett. 7 (2005) 5569-5572
13. For consistency the spiculoic acid numbering scheme will be used through the body of the text. Systematic names and numbering will be used in the experimental.
14. Kirkham J.E., Lee V., and Baldwin J.E. Org. Lett. 8 (2006) 5537-5540
15. Kirkham J.E., Lee V., and Baldwin J.E. Chem. Commun. (2006) 2863-2865
16. Paterson I., Wallace D.J., and Velazquez S.M. Tetrahedron Lett. 35 (1994) 9083-9086
17. Paterson I., and Wallace D.J. Tetrahedron Lett. 35 (1994) 9087-9090
18. Paterson I., Wallace D.J., and Cowden C.J. Synthesis (1998) 639-652
19. Roush W.R. J. Org. Chem. 56 (1991) 4151-4157
20. Smith A.B.I., Beaucham T.J., LaMarche M.J., Kaufman M.D., Qiu Y., Arimoto H., Jones D.R., and Kobayashi K. J. Am. Chem. Soc. 122 (2000) 8654-8664
21. Corey E.J., Cho H., Rucker C., and Hua D.H. Tetrahedron Lett. 22 (1981) 3455-3458
22. McDonald R.N., and Campbell T.W. J. Org. Chem. 24 (1959) 1969-1975
23. Onaran M.B., and Seto C.T. J. Org. Chem. 68 (2003) 8136-8141
24. Yadav V.K., and Babu K.G. Tetrahedron 59 (2003) 9111-9116
25. Gaukroger K., Hadfield J.A., Hepworth L.A., Lawrence N.J., and McGown A.T. J. Org. Chem. 66 (2001) 8135-8138
26. Benson S.W., Egger K.W., and Golden D.M. J. Am. Chem. Soc. 87 (1965) 468-476
27. Dickinson R.G., and Lotzkar H. J. Am. Chem. Soc. 59 (1937) 472-476
28. Tanemura K., Suzuki T., and Horaguchi T. J. Chem. Soc., Chem. Commun. (1992) 979-980
29. Wang Y., Babirad S.A., and Kishi Y. J. Org. Chem. 57 (1992) 468-481
30. Onoda T., Shirai R., and Iwasaki S. Tetrahedron Lett. 38 (1997) 1443-1446
31. Mancuso A.J., Huang S.-L., and Swern D. J. Org. Chem. 43 (1978) 2480-2482
32. Desert S., and Metzner P. Tetrahedron 48 (1992) 10327-10338
33. Lister T., and Perkins M.V. Aust. J. Chem. 57 (2004) 787-797
34. Crossman, J. S. Ph.D. Thesis, Flinders University, 2007.
35. Crimmins M.T., King B.W., Tabet E.A., and Chadhary K. J. Org. Chem. 66 (2001) 894-902
36. Velazquez F., and Olivo H.F. Curr. Org. Chem. 6 (2002) 303-340
37. Crimmins M.T., and King B.W. J. Am. Chem. Soc. 120 (1998) 9084-9085
38. Nicolaou K.C., Petasis N.A., Zipkin R.E., and Uenishi J. J. Am. Chem. Soc. 104 (1982) 5555-5557
39. Blakemore P.R., Cole W.J., Kocienski P.J., and Morley A. Synlett (1998) 26-28
40. Evans D.A., Ng H.P., and Rieger D.L. J. Am. Chem. Soc. 115 (1993) 11446-11459
41. Newton R.F., Reynolds D.P., Finch M.A.W., Kelly D.R., and Roberts S.M. Tetrahedron Lett. 41 (1979) 3981-3982
42. Williams D.H., and Fleming I. Spectroscopic Methods in Organic Chemistry. 5th ed. (2004), Tata McGraw Hill, New Delhi