Microwave enabled external carboxymethyl substituents in the ring-closing metathesis

Tetrahedron Letters

Volumn 44, Issue 9, 2003, Pages 1783-1786

  Yang, Cangming ^a   Murray, William V ^a   Wilson, Lawrence J ^a  

^a JOHNSON AND JOHNSON PHARMACEUTICAL RESEARCH AND DEVELOPMENT   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKADIENE; CYCLOPENTENE DERIVATIVE; FURAN DERIVATIVE; PYRROLE DERIVATIVE;

ALKYLATION; ARTICLE; DECOMPOSITION; MICROWAVE IRRADIATION; OXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; RING CLOSING METATHESIS; TEMPERATURE;

EID: 0037463511     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)00083-2     Document Type: Article

References (20)

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2. Trnka T.M., Grubbs R.H. Acc. Chem. Res. 34:2001;18-29.
3. Recent examples: (+)-Laurencin: Crimmins, M. T.; Choy, A. L. J. Am. Chem. Soc. 1999, 121, 5653-5660; Sarain A: Irie, O.; Samizu, K.; Henry, J. R.; Weinreb, S. M. J. Org. Chem. 1999, 64, 587-595; (-)-Fumagillol: Boiteau, J. G.; Van de Weghe, P.; Eustache, J. Org. Lett. 2001, 3, 2737-2740; Octalactin A: Buszek, K. R.; Sato, N.; Jeong, Y. Tetrahedron Lett. 2002, 43, 181-184; Amphidinolide A: Maleczka, R. E.; Terrell, L. R.; Geng, F.; Ward, J. S. Org. Lett. 2002, 4, 2841-2844; (-)-Pinolidoxin: Liu, D.; Kozmin, S. A. Org. Lett. 2002, 4, 3005-3007.
4. Recent examples: (+)-Laurencin: Crimmins, M. T.; Choy, A. L. J. Am. Chem. Soc. 1999, 121, 5653-5660; Sarain A: Irie, O.; Samizu, K.; Henry, J. R.; Weinreb, S. M. J. Org. Chem. 1999, 64, 587-595; (-)-Fumagillol: Boiteau, J. G.; Van de Weghe, P.; Eustache, J. Org. Lett. 2001, 3, 2737-2740; Octalactin A: Buszek, K. R.; Sato, N.; Jeong, Y. Tetrahedron Lett. 2002, 43, 181-184; Amphidinolide A: Maleczka, R. E.; Terrell, L. R.; Geng, F.; Ward, J. S. Org. Lett. 2002, 4, 2841-2844; (-)-Pinolidoxin: Liu, D.; Kozmin, S. A. Org. Lett. 2002, 4, 3005-3007.
5. Recent examples: (+)-Laurencin: Crimmins, M. T.; Choy, A. L. J. Am. Chem. Soc. 1999, 121, 5653-5660; Sarain A: Irie, O.; Samizu, K.; Henry, J. R.; Weinreb, S. M. J. Org. Chem. 1999, 64, 587-595; (-)-Fumagillol: Boiteau, J. G.; Van de Weghe, P.; Eustache, J. Org. Lett. 2001, 3, 2737-2740; Octalactin A: Buszek, K. R.; Sato, N.; Jeong, Y. Tetrahedron Lett. 2002, 43, 181-184; Amphidinolide A: Maleczka, R. E.; Terrell, L. R.; Geng, F.; Ward, J. S. Org. Lett. 2002, 4, 2841-2844; (-)-Pinolidoxin: Liu, D.; Kozmin, S. A. Org. Lett. 2002, 4, 3005-3007.
6. Recent examples: (+)-Laurencin: Crimmins, M. T.; Choy, A. L. J. Am. Chem. Soc. 1999, 121, 5653-5660; Sarain A: Irie, O.; Samizu, K.; Henry, J. R.; Weinreb, S. M. J. Org. Chem. 1999, 64, 587-595; (-)-Fumagillol: Boiteau, J. G.; Van de Weghe, P.; Eustache, J. Org. Lett. 2001, 3, 2737-2740; Octalactin A: Buszek, K. R.; Sato, N.; Jeong, Y. Tetrahedron Lett. 2002, 43, 181-184; Amphidinolide A: Maleczka, R. E.; Terrell, L. R.; Geng, F.; Ward, J. S. Org. Lett. 2002, 4, 2841-2844; (-)-Pinolidoxin: Liu, D.; Kozmin, S. A. Org. Lett. 2002, 4, 3005-3007.
7. Recent examples: (+)-Laurencin: Crimmins, M. T.; Choy, A. L. J. Am. Chem. Soc. 1999, 121, 5653-5660; Sarain A: Irie, O.; Samizu, K.; Henry, J. R.; Weinreb, S. M. J. Org. Chem. 1999, 64, 587-595; (-)-Fumagillol: Boiteau, J. G.; Van de Weghe, P.; Eustache, J. Org. Lett. 2001, 3, 2737-2740; Octalactin A: Buszek, K. R.; Sato, N.; Jeong, Y. Tetrahedron Lett. 2002, 43, 181-184; Amphidinolide A: Maleczka, R. E.; Terrell, L. R.; Geng, F.; Ward, J. S. Org. Lett. 2002, 4, 2841-2844; (-)-Pinolidoxin: Liu, D.; Kozmin, S. A. Org. Lett. 2002, 4, 3005-3007.
8. Recent examples: (+)-Laurencin: Crimmins, M. T.; Choy, A. L. J. Am. Chem. Soc. 1999, 121, 5653-5660; Sarain A: Irie, O.; Samizu, K.; Henry, J. R.; Weinreb, S. M. J. Org. Chem. 1999, 64, 587-595; (-)-Fumagillol: Boiteau, J. G.; Van de Weghe, P.; Eustache, J. Org. Lett. 2001, 3, 2737-2740; Octalactin A: Buszek, K. R.; Sato, N.; Jeong, Y. Tetrahedron Lett. 2002, 43, 181-184; Amphidinolide A: Maleczka, R. E.; Terrell, L. R.; Geng, F.; Ward, J. S. Org. Lett. 2002, 4, 2841-2844; (-)-Pinolidoxin: Liu, D.; Kozmin, S. A. Org. Lett. 2002, 4, 3005-3007.
9. Fu G.C., Nguyen S.T., Grubbs R.H. J. Am. Chem. Soc. 115:1993;9856-9857.
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12. Basu K., Cabral J.A., Paquette L.A. Tetrahedron Lett. 43:2002;5453-5456.
13. Mayo K.G., Nearhoof E.H., Kiddle J.J. Org. Lett. 4:2002;1567-1570.
14. All microwave reactions were performed in the CEM Discover™ unit produced by the CEM Corporation, Mathews, N.C. Settings and readings for power (W), time of irradiation, and pressure were taken from the instrument. Reactions were performed in an 8 mL sealed vessel equipped with a Teflon stir flea. The vessels were sealed with septa and aluminum crimp provided by the vendor.
15. 13C NMR/DEPT spectra consistent with the structural assignments.
16. 2), 127.85 (CH), 130.32 (CH), 136.47 (CH); MS (ESI): 585 (2M+23), 304 (M+23), 282 (M+H).
17. General procedure for microwave-assisted RCM products in Table 2. Substrate (4a-f) was dissolved in 4 mL of 1,2-dichloroethane in a pressure tube containing a magnetic stir bar to yield solutions with a concentration between 0.025 and 0.05 M. The catalyst (2) was then weighed into the pressure tube. The pressure tube was then sealed and heated under selected microwave conditions. The reaction conversion was monitored and analyzed by LC/MS. The solvent was removed by rotary evaporator, and the crude product was purified by flash chromatography (hexane/ethyl acetate=9/1 for entries 1 and 2; hexane/ethyl acetate=20/1 for entries 4 and 6; hexane/ethyl acetate=100/1 for entry 5; methylene chloride for entry 3).
18. 3/CH), 110.44 (CH), 121.23 (CH), 125.06 (CH), 126.33 (CH), 128.3 (CH), 129.22 (CH); MS (ESI): 481 (2M+23), 230 (M+H).
19. To our knowledge, this system has not been prepared or reported. The pyrrolidine-3-carboxylate has been utilized as a β-turn motif in a GPIIb/IIIa antagonist, see: Hoekstra, W. J.; Maryanoff, B. E.; Damiano, B. P.; Andrade-Gordon, P.; Cohen, J. H.; Costanzo, M. J.; Haertlein, B. J.; Hecker, L. R.; Hulshizer, B. L.; Kauffman, J. A.; Keane, P.; McComsey, D. F.; Mitchell, J. A.; Scott, L.; Shah, R. D.; Yabut, S. C. J. Med. Chem. 1999, 42, 5254-5265.
20. The 1,2-dehydro variant has been utilized in an intramolecular Diels-Alder approach to the galanthan ring system, see: Morgans D.J., Stork G. Tetrahedron Lett. 20:1979;1959-1962.