Enantioselective synthesis of (R)-incrustoporin, an antibiotic isolated from Incrustoporia carneola

Tetrahedron Asymmetry

Volumn 10, Issue 6, 1999, Pages 1163-1172

  Rossi, Renzo ^a   Bellina, Fabio ^a   Biagetti, Matteo ^a   Mannina, Luisa ^b  

^a UNIVERSITY OF PISA   (Italy)

^b UNIVERSITY OF MOLISE   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIBIOTIC AGENT; INCRUSTOPORIN; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOMER; HYDROGENATION; PHYSICAL CHEMISTRY; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 0033605624     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(99)00085-3     Document Type: Article

References (31)

1. (a) Rossi, R.; Bellina, F.; Mannina, L. Tetrahedron Lett. 1998, 39, 3017;
2. (b) Rossi, R.; Bellina, F.; Biagetti, M.; Mannina, L. Tetrahedron Lett. 1998, 39, 7599;
3. (c) Rossi, R.; Bellina, F.; Biagetti, M.; Mannina, L. Tetrahedron Lett. 1998, 39, 7799;
4. (d) Rossi, R.; Bellina, F.; Biagetti, M. Synth. Commun. in press.
5. Zapf, S.; Anke, T.; Sterner, O. Acta Chem. Scand. 1995, 49, 233.
6. Yajima, A.; Mori, K. Liebigs Ann. Chem. 1996, 1091.
7. For the synthesis of enantiomerically enriched 3,5-disubstituted 5H-furan-2-ones starting from enantiomerically enriched propargylic mesylates, see: Marshall, J. A.; Wolf, M. A.; Wallace, E. M. J. Org. Chem. 1997, 62, 367.
8. For the synthesis of (R)-3-alkyl-5-methyl-5H-furan-2-ones by retro-Diels-Alder reaction of the adducts from cyclopentadiene and (R)-angelica lactone, see: Corber, J.; Font, J.; Monsalvatje, M.; Ortuno, R. M.; Sanchez-Ferrando, F. J. Org. Chem. 1988, 53, 4393.
9. For the synthesis of the chiral non-racemic 3-substituted 5-methyl-5H-furan-2-one moiety of annonaceous acetogenins by a CpRu(COD)Cl-catalyzed annulation on a monosubstituted carbon-carbon double bond with enantiomerically pure ethyl (S)-4-hydroxypentynoate, see: (a) Trost, B. M.; Müller, T. J. J.; Martinez, J. J. Am. Chem. Soc. 1995, 117, 1888; (b) Trost, B. M.; Shi, Z. J. Am. Chem. Soc. 1994, 116, 7459.
10. For the synthesis of the chiral non-racemic 3-substituted 5-methyl-5H-furan-2-one moiety of annonaceous acetogenins by a CpRu(COD)Cl-catalyzed annulation on a monosubstituted carbon-carbon double bond with enantiomerically pure ethyl (S)-4-hydroxypentynoate, see: (a) Trost, B. M.; Müller, T. J. J.; Martinez, J. J. Am. Chem. Soc. 1995, 117, 1888; (b) Trost, B. M.; Shi, Z. J. Am. Chem. Soc. 1994, 116, 7459.
11. For the synthesis of the chiral non-racemic 3-substituted 5-methyl-5H-furan-2-one moiety and annonaceous acetogenins starting from L-lactic acid derivatives, see: (a) Yao, Z.-J.; Wu, Y.-L. J. Org. Chem. 1995, 60, 1170; (b) Makabe, H.; Tanaka, A.; Oritani, T. J. Chem. Soc., Perkin Trans. 1 1994, 1975; (c) Yao, Z.-J.; Yu, Q.; Wu, Y.-L. Synth. Commun. 1996, 26, 3613; (d) Sinha, S. C.; Keinan, E. J. Am. Chem. Soc. 1993, 115, 4891.
12. For the synthesis of the chiral non-racemic 3-substituted 5-methyl-5H-furan-2-one moiety and annonaceous acetogenins starting from L-lactic acid derivatives, see: (a) Yao, Z.-J.; Wu, Y.-L. J. Org. Chem. 1995, 60, 1170; (b) Makabe, H.; Tanaka, A.; Oritani, T. J. Chem. Soc., Perkin Trans. 1 1994, 1975; (c) Yao, Z.-J.; Yu, Q.; Wu, Y.-L. Synth. Commun. 1996, 26, 3613; (d) Sinha, S. C.; Keinan, E. J. Am. Chem. Soc. 1993, 115, 4891.
13. For the synthesis of the chiral non-racemic 3-substituted 5-methyl-5H-furan-2-one moiety and annonaceous acetogenins starting from L-lactic acid derivatives, see: (a) Yao, Z.-J.; Wu, Y.-L. J. Org. Chem. 1995, 60, 1170; (b) Makabe, H.; Tanaka, A.; Oritani, T. J. Chem. Soc., Perkin Trans. 1 1994, 1975; (c) Yao, Z.-J.; Yu, Q.; Wu, Y.-L. Synth. Commun. 1996, 26, 3613; (d) Sinha, S. C.; Keinan, E. J. Am. Chem. Soc. 1993, 115, 4891.
14. For the synthesis of the chiral non-racemic 3-substituted 5-methyl-5H-furan-2-one moiety and annonaceous acetogenins starting from L-lactic acid derivatives, see: (a) Yao, Z.-J.; Wu, Y.-L. J. Org. Chem. 1995, 60, 1170; (b) Makabe, H.; Tanaka, A.; Oritani, T. J. Chem. Soc., Perkin Trans. 1 1994, 1975; (c) Yao, Z.-J.; Yu, Q.; Wu, Y.-L. Synth. Commun. 1996, 26, 3613; (d) Sinha, S. C.; Keinan, E. J. Am. Chem. Soc. 1993, 115, 4891.
15. For the synthesis of the chiral non-racemic 3-substituted 5-methyl-5H-furan-2-one moiety of annonaceous acetogenins starting from (S)-1,2-epoxybutane, see: (a) Thi, T. V.; Chaboche, C.; Figadère, B.; Chappe, B.; Chi, H. B.; Cavé, A. Tetrahedron Lett. 1994, 35, 883; (b) Hoye, T. R.; Hanson, P. R. Tetrahedron Lett. 1993, 34, 5043; (c) Hoye, T. R.; Ye, Z. J. Am. Chem. Soc. 1996, 118, 1801; (d) Franck, X.; Figadère, B.; Cavé, A. Tetrahedron Lett. 1996, 37, 1593.
16. For the synthesis of the chiral non-racemic 3-substituted 5-methyl-5H-furan-2-one moiety of annonaceous acetogenins starting from (S)-1,2-epoxybutane, see: (a) Thi, T. V.; Chaboche, C.; Figadère, B.; Chappe, B.; Chi, H. B.; Cavé, A. Tetrahedron Lett. 1994, 35, 883; (b) Hoye, T. R.; Hanson, P. R. Tetrahedron Lett. 1993, 34, 5043; (c) Hoye, T. R.; Ye, Z. J. Am. Chem. Soc. 1996, 118, 1801; (d) Franck, X.; Figadère, B.; Cavé, A. Tetrahedron Lett. 1996, 37, 1593.
17. For the synthesis of the chiral non-racemic 3-substituted 5-methyl-5H-furan-2-one moiety of annonaceous acetogenins starting from (S)-1,2-epoxybutane, see: (a) Thi, T. V.; Chaboche, C.; Figadère, B.; Chappe, B.; Chi, H. B.; Cavé, A. Tetrahedron Lett. 1994, 35, 883; (b) Hoye, T. R.; Hanson, P. R. Tetrahedron Lett. 1993, 34, 5043; (c) Hoye, T. R.; Ye, Z. J. Am. Chem. Soc. 1996, 118, 1801; (d) Franck, X.; Figadère, B.; Cavé, A. Tetrahedron Lett. 1996, 37, 1593.
18. For the synthesis of the chiral non-racemic 3-substituted 5-methyl-5H-furan-2-one moiety of annonaceous acetogenins starting from (S)-1,2-epoxybutane, see: (a) Thi, T. V.; Chaboche, C.; Figadère, B.; Chappe, B.; Chi, H. B.; Cavé, A. Tetrahedron Lett. 1994, 35, 883; (b) Hoye, T. R.; Hanson, P. R. Tetrahedron Lett. 1993, 34, 5043; (c) Hoye, T. R.; Ye, Z. J. Am. Chem. Soc. 1996, 118, 1801; (d) Franck, X.; Figadère, B.; Cavé, A. Tetrahedron Lett. 1996, 37, 1593.
19. For the synthesis of naturally occurring (+)-1,11-dodecadien-1-yl-5-methyl-5H-furan-2-one (hamabiwa-lactone B) from (2RS,4S)-4-methyl-2-phenylsulfanyl-γ-butyrolactone, see: Richecoeur, A. M. E.; Sweeney, J. B. Tetrahedron Lett. 1998, 39, 8901.
20. Yu, W-Y.; Alper, H. J. Org. Chem. 1997, 62, 5684.
21. (a) Matsumura, K.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1997, 119, 8738 and references cited therein;
22. (b) Midland, M. M.; McDowell, D. C.; Hatch, R. L.; Tramontano, A. J. Am. Chem. Soc. 1980, 102, 867;
23. (c) Bach, J.; Berenguer, R.; Garcia, J.; Loscertales, T.; Villarosa, J. J. Org. Chem. 1996, 61, 9021;
24. (d) Singh, V. K. Synthesis 1992, 605 and references cited therein.
25. Negishi, E.; Kotora, M.; Xu, C. J. Org. Chem. 1997, 62, 8957.
26. Ramachandran, P. V.; Teodorovic', A. V.; Rangaishenvi, M. L.; Brown, H. C. J. Org. Chem. 1992, 57, 2379.
27. (a) Midland, M. M.; Zderic, S. A. J. Am. Chem. Soc. 1982, 104, 525;
28. (b) Tramontano, A.; Zderic, S. A. J. Organomet. Chem. 1978, 156, 203.
29. El-Ali, B.; Alper, H. J. Org. Chem. 1991, 56, 5357.
30. Coulson, D. R. Inorg. Synth. 1971, 13, 121.
31. Halle, R.; Bréherét, A.; Schulz, E.; Pinel, C.; Lemaire, M. Tetrahedron: Asymmetry 1997, 8, 2101.