Synthesis of butenolides recently isolated from marine microorganisms

Tetrahedron Letters

Volumn 48, Issue 44, 2007, Pages 7878-7881

  Karlsson, Staffan ^a   Andersson, Fredrik ^b   Breistein, Palle ^b   Hedenström, Erik ^b  

^a ASTRAZENECA R AND D   (Sweden)

^b MID SWEDEN UNIVERSITY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

1,2 EPOXY 3 BUTENE; 4,11 DIHYDROXY 10 METHYL DODEC 2 EN 1,4 OLIDE; BUTENOLIDE; CAMPHOR DERIVATIVE; CAMPHORSULTAM; CARBONYL DERIVATIVE; LITHIUM; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; CYCLOADDITION; DIASTEREOISOMER; ENANTIOMER; MARINE SPECIES; MITSUNOBU REACTION; NONHUMAN; REACTION ANALYSIS; RING CLOSING METATHESIS; RING OPENING; STREPTOMYCETE B 5632; STREPTOVERTICILLIUM LUTEOVERTICILLATUM; STRUCTURE ANALYSIS; SYNTHESIS;

STREPTOMYCES LUTEOVERTICILLATUS;

EID: 34848845804     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.08.123     Document Type: Article

References (40)

1. See for example:. Smith C.J., Abbanat D., Bernan V.S., Maiese W.M., Greenstein M., Jompa J., Tahir A., and Ireland C.M. J. Nat. Prod. 63 (2000) 142-145
2. Guo Y.-W., Gavagnin M., Mollo E., Trivellone E., and Cimino G. J. Nat. Prod. 62 (1999) 1194-1196
3. Rodríguez A.B., and Ramírez C. J. Nat. Prod. 57 (1994) 339-347
4. Braun D., Pauli N., Séquin U., and Zhäner H. FEMS Microbiol. Lett. 126 (1995) 37-42
5. Yamada Y., and Nihira T. In: Barton D., and Nakanishi K. (Eds). Comprehensive Natural Product Chemistry Vol. 8 (1999), Elsevier, Oxford 377-413
6. Sakuda S., Tanaka S., Mizuno K., Sukcharoen O., Nihira T., and Yamada Y. J. Chem. Soc., Perkin Trans. 1 (1993) 2309-2315
7. Ishigami K., and Kitahara T. Tetrahedron 51 (1995) 6431-6442
8. Pawlick J.R., and Fenical W. Mar. Ecol. Prog. Ser. 87 (1992) 183-188
9. Mukku V.J.R.V., Speitling M., Laatsch H., and Helmke E. J. Nat. Prod. 63 (2000) 1570-1572
10. Li D.-H., Zhu T.-J., Liu H.-B., Fang Y.-C., Gu Q.-Q., and Zhu W.-M. Arch. Pharm. Res. 29 (2006) 624-626
11. See for example:. Nakamura Y., and Mori K. Eur. J. Org. Chem. (1999) 2175-2182
12. Larsson M., Nguyen B.-V., Högberg H.-E., and Hedenström E. Eur. J. Org. Chem. (2001) 353-363
13. Tai A., Higashiura Y., Kakizaki M., Naito T., Tanaka K., Fujita M., Sugimura T., Hara H., and Hayashi N. Biosci. Biotechnol. Biochem. 62 (1998) 607-608
14. De Marino S., Iorizzi M., Palagiano E., Zollo F., and Roussakis C. J. Nat. Prod. 61 (1998) 1319-1327
15. Middleton R.F., Foster G., Cannel R.J.P., Sidebottom P.J., Taylor N.L., Noble D., Todd M., Dawson M.J., and Lawrence G.C. J. Antibiot. 48 (1995) 311-316
16. Karlsson S., and Högberg H.-E. Org. Lett. 1 (1999) 1667-1669
17. Karlsson S., and Högberg H.-E. Synthesis (2000) 1863-1867
18. See for example:. Hanessian S., Roy P.J., Petrini M., Hodges P.J., Di Fabio R., and Carganico G. J. Org. Chem. 55 (1990) 5766-5777
19. de March P., Figueredo M., Font J., Raya J., Alvarez-Larena A., and Piniella J.F. J. Org. Chem. 68 (2003) 2437-2447
20. Konno H., Makabe H., Tanaka A., and Oritani T. Tetrahedron Lett. 37 (1996) 5393-5396
21. Zask A. J. Org. Chem. 57 (1992) 4558-4560
22. Dehoux C., Gorrichon L., and Baltas M. Eur. J. Org. Chem. (2001) 1105-1113
23. Trost B.M., and Müller T.J.J. J. Am. Chem. Soc. 116 (1994) 4985-4986
24. RCM as a key step. See for example:. Anand R.V., Baktharaman S., and Singh V.K. Tetrahedron Lett. 43 (2002) 5393-5395
25. Carda M., Rodríguez S., González F., Castillo E., Villanueva A., and Marco J.A. Eur. J. Org. Chem. (2002) 2649-2655
26. Fürstner A., and Dierkes T. Org. Lett. 2 (2000) 2463-2465
27. See for example:. Fürstner A., Seidel G., and Kindler N. Tetrahedron 55 (1999) 8215-8230
28. Armstrong S.K., and Christie B.A. Tetrahedron Lett. 37 (1996) 9373-9376
29. Shon Y.-S., and Lee T.R. Tetrahedron Lett. 38 (1997) 1283-1286
30. Mascareñas J.L., Rumbo A., and Castedo L. J. Org. Chem. 62 (1997) 8620-8621
31. Stork G., and Zhao K. Tetrahedron Lett. 30 (1989) 287-290
32. Trnka T.M., and Grubbs R.H. Acc. Chem. Res. 34 (2001) 18-29 and references cited therein
33. See for example:. Ghosh A.K., Cappiello J., and Shin D. Tetrahedron Lett. 39 (1998) 4651-4654
34. Fürstner A., and Langemann K. J. Am. Chem. Soc. 119 (1997) 9130-9136
35. Williams D.R., Brown D.L., and Benbow J.W. J. Am. Chem. Soc. 111 (1989) 1923-1925
36. 3) 225.1496.
37. Razikin J., González A., and Gil P. Tetrahedron: Asymmetry 7 (1996) 3479-3484
38. 3) 225.1496.
39. 3) 225.1496.
40. 3) 225.1496.