Stereoselective synthesis of dihydropyrone-containing marine natural products. Total synthesis and structural elucidation of (-)-membrenone-C

Organic Letters

Volumn 3, Issue 1, 2001, Pages 123-125

  Perkins, Michael V ^a   Sampson, Rebecca A ^a  

^a FLINDERS UNIVERSITY   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

BIOLOGICAL PRODUCT; MEMBRENONE A; MEMBRENONE B; MEMBRENONE C; PYRONE DERIVATIVE;

ANIMAL; ARTICLE; BIOLOGY; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; COMPARATIVE STUDY; DEHYDRATION; MOLLUSC; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOISOMERISM; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

ANIMALS; BIOLOGICAL PRODUCTS; CATALYSIS; DEHYDRATION; MAGNETIC RESONANCE SPECTROSCOPY; MARINE BIOLOGY; MOLECULAR STRUCTURE; MOLLUSCA; PYRONES; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0035843281     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol006835w     Document Type: Article

References (22)

1. Ciavatta, M. L.; Trivellone, E.; Villani, G.; Cimino, G. Tetrahedron Lett. 1993, 34, 6791.
2. Perkins, M. V.; Sampson, R. A. Tetrahedron Lett. 1998, 39, 8367.
3. (a) Paterson, I. Pure Appl. Chem. 1992, 64, 1821-30.
4. (b) Paterson, I.; Perkins, M. V. Tetrahedron Lett. 1992, 33, 801.
5. (c) Paterson, I.; Channon, J. A. Tetrahedron Lett. 1992, 33, 797.
6. (d) Paterson, I.; Perkins, M. V. Tetrahedron 1996, 52, 1811.
7. (e) Paterson, I.; Norcross, R. D.; Ward, R. A.; Romea, P.; Lister, M. A. J. Am. Chem. Soc. 1994, 116, 11287.
8. (f) Paterson, I.; Cumming, J. G.; Ward, R. A.; Lamboley, S. Tetrahedron 1995, 51, 9393.
9. (g) Paterson, I.; Schlapbach, A. Synlett 1995, 498.
10. (a) Evans, D. A.; Clark, J. S.; Metternich, R.; Novak, V. J.; Sheppard, G. S. J. Am. Chem. Soc. 1990, 112, 866.
11. (b) Evans, D. A.; Urpí, F.; Somers, T. C.; Clark, J. S.; Bilodeau, M. T. J. Am. Chem. Soc. 1990, 112, 8215.
12. (c) Evans, D. A.; Riegler, D. L.; Bilodeau, M. T.; Urpi, F. J. Am. Chem. Soc. 1991, 113, 1047.
13. Paterson, I.; Tillyer, R. D. Tetrahedron Lett 1992, 33, 4233.
14. (a) Narasaka, K.; Pai, F.-C. Tetrahedron 1984, 40, 2233.
15. (b) Paterson, I.; Donghi, M.; Gerlach, K. Angew. Chem., Int. Ed. 2000, 39, 3315.
16. (a) Trost, B. M.; Caldwell, C. G. Tetrahedron Lett. 1981, 22, 4999.
17. (b) Corey, E. J.; Hopkins, P. B. Tetrahedron Lett. 1982, 23, 4871.
18. (c) Trost, B. M.; Caldwell, C. G.; Murayama, E.; Heissler, D. J. Org. Chem. 1983, 48, 3252.
19. The natural product was reported (ref 1) as an oil, presumably as a result of the small amount isolated (3 mg).
20. 13C NMR spectrum match except for the signal reported (ret 1) at δ = 81.74 ppm, which was found to occur at δ = 80.93 ppm, and the signal at δ = 83.05 ppm, which was found to occur at δ = 81.69 ppm. We cannot explain this discrepancy, but the identity of all of the other signal confirms the stereochemical assignment.
21. 3).
22. Evans, D. A.; Kaldor, S. W.; Jones, T. K.; Clardy, J.; Stout, T. J. J. Am. Chem. Soc. 1990, 112, 7001.