A short olefin metathesis-based route to enantiomerically pure arylated dihydropyrans and α,β-unsaturated δ-valero lactones

Journal of Organic Chemistry

Volumn 68, Issue 3, 2003, Pages 799-804

  Wildemann, Holger ^a   Dünkelmann, Pascal ^b   Müller, Michael ^b   Schmidt, Bernd ^a  

^a TU DORTMUND UNIVERSITY   (Germany)

^b FORSCHUNGSZENTRUM JÜLICH   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CONDENSATION; ENZYMES; RING OPENING POLYMERIZATION;

METATHESIS-BASED ROUTE;

OLEFINS;

2 METHYL 3 PHENYL 3,6 DIHYDRO 2H PYRAN 3 OL; 2,3 BIS(4 BROMOPHENYL) 3,6 DIHYDRO 2H PYRAN 3 OL; 2,3 DIPHENYL 3,6 DIHYDRO 2H PYRAN 3 OL; 5 (3 CHLOROPHENYL) 5 HYDROXY 6 METHYL 5,6 DIHYDROPYRAN 2 ONE; ADRENERGIC RECEPTOR STIMULATING AGENT; HETEROCYCLIC COMPOUND; KETONE; LACTONE; LEUKOTRIENE RECEPTOR BLOCKING AGENT; PIPERIDINE DERIVATIVE; PYRAN DERIVATIVE; RUTHENIUM; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; DIASTEREOISOMER; ENANTIOMER; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; RING CLOSING METATHESIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0348209611     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0264729     Document Type: Article

References (28)

1. Crawley, G. C.; Dowell, R. I.; Edwards, P. N.; Foster, S. J.; McMillan, R. M.; Walker, E. R. H.; Waterson, D. J. Med. Chem. 1992, 35, 2600-2609.
2. Kulagowski, J. J.; Curtis, N. R.; Swain, C. J.; Williams, B. J. Org. Lett. 2001, 3, 667-670.
3. Wallace, D. J.; Goodman, J. M.; Kennedy, D. J.; Davies, A. J.; Cowden, C. J.; Ashwood, M. S.; Cottrell, I. F.; Dolling, U.-H.; Reider, P. J. Org. Lett. 2001, 3, 671-674.
4. Petukhov, P. A.; Zhang, J. R.; Kozikowski, A. P.; Wang, C. Z.; Ye, Y. P.; Johnson, K. M.; Tella, S. R. J. Med. Chem. 2002, 45, 3161-3170.
5. Amat, M.; Cantó, M.; Llor, N.; Escolano, C.; Molins, E.; Espinosa, E.; Bosch, J. J. Org. Chem. 2002, 67, 5343-5351.
6. Smitrovich, J. H.; Boice, G. N.; Qu, C.; DiMichele, L.; Nelson, T. D.; Huffman, M. A.; Murry, J.; McNamara, J.; Reider, P. J. Org. Lett. 2002, 4, 1963-1966.
7. Macchia, B.; Balsamo, A.; Epifani, E.; Lapucci, A.; Nencetti, S.; Macchia, F.; Breschi, M. C.; Martinotti, E.; Ceserani, R. J. Med. Chem. 1986, 29, 740-747.
8. Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371-388.
9. Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413-4450.
10. Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2036-2055.
11. Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3013-3043.
12. Demir, A. S.; Pohl, M.; Janzen, E.; Müller, M. J. Chem. Soc., Perkin Trans. 1 2001, 633-635.
13. Demir, A. S.; Sesenoglu, Ö.; Eren, E.; Hosrik, B.; Pohl, M.; Janzen, E.; Kolter, D.; Feldmann, R.; Dünkelmann, P.; Müller, M. Adv. Synth. Catal. 2002, 344, 96-103.
14. Demir, A. S.; Dünnwald, T.; Iding, H.; Pohl, M.; Müller, M. Tetrahedron: Asymmetry 1999, 10, 4769-4774.
15. Iding, H.; Dünnwald, T.; Greiner, L.; Liese, A.; Müller, M.; Siegert, P.; Grötzinger, J.; Demir, A. S.; Pohl, M. Chem. Eur. J. 2000, 6, 1483-1495.
16. Aurich, H. G.; Biesemeier, F.; Boutahar, M. Chem. Ber. 1991, 124, 2329-2334.
17. Schmidt, B.; Wildemann, H. J. Chem. Soc., Perkin Trans. 1 2000, 2916-2925.
18. Fürstner, A.; Langemann, K. Synthesis 1997, 792-803.
19. Scholl, M.; Trnka, T. M.; Morgan, J. P.; Grubbs, R. H. Tetrahedron Lett. 1999, 40, 2247-2250.
20. Fürstner, A.; Thiel, O. R.; Kindler, N.; Bartkowska, B. J. Org. Chem. 2000, 65, 7990-7995.
21. Held, C.; Fröhlich, R.; Metz, P. Angew. Chem., Int. Ed. 2001, 40, 1058-1060.
22. Fürstner, A.; Ackermann, L.; Gabor, B.; Goddard, R.; Lehmann, C. W.; Mynott, R.; Stelzer, F.; Thiel, O. R. Chem. Eur. J. 2001, 7, 3236-3253.
23. Schmidt, B.; Pohler, M.; Costisella, B. Tetrahedron 2002, 58, 7951-7958.
24. Cram, D. J.; Wilson, D. R. J. Am. Chem. Soc. 1963, 85, 1245-1249.
25. Chen, X.; Hortelano, E. R.; Eliel, E. L.; Frye, S. V. J. Am. Chem. Soc. 1992, 114, 1778-1784.
26. Reetz, M. T. Angew. Chem., Int. Ed. Engl. 1984, 23, 556-569.
27. Schwab, P.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1996, 118, 100-110.
28. Scholl, M.; Ding, S.; Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953-956.