Synthesis of fused tricyclic β-lactams by the Pauson-Khand cyclization of enyne-2-azetidinones

Tetrahedron Letters

Volumn 37, Issue 38, 1996, Pages 6901-6904

  Alcaide, Benito ^a   Polanco, Concepción ^a   Sierra, Miguel A ^a  

^a UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

BETA LACTAM DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0030590508     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01511-0     Document Type: Article

References (40)

1. 1. For reviews on the P-K reaction see, for example: (a) Schore, N. E. in Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I.; Eds. Pergamon Press: Oxford, U.K. 1991; vol. 5, pp. 1037-1064.
2. (b) Schore, N. E. Organic Reactions 1991, 40, 1-90.
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4. 2. Perboni, A.; Tamburini, B.; Rossi, T.; Donati, D.; Tarzia, G.; Gaviraghi, G. In Recent Advances in Chemistry of Anti-Infective Agents; Bentley, P.H. Ponsford, R. Eds.; The Royal Society of Chemistry, Cambridge, UK, 1992, pp 21-35
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11. 4. Some recent references: (a) Banik, B. K.; Subbaraju, G. V.; Manhas, M. S.; Bose, A. K. Tetrahedron Lett. 1996, 37, 1363-1366.
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13. 5. Enantiomerically pure 2-azetidinones 4a-b are obtained from the corresponding protected D-gliceraldehyde acetonide imines, 3c-d, through Staüdinger reaction with benzyloxyacetyl chloride as single cis-enantiomers. The stereochemical outcome of this type of β-lactams has been determined both experimental and theoretically. For the experimental approach see: (a) Hubschwerelen, C.; Schmid, G. Helv. Chim. Acta 1983, 66, 2206.
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16. For the theoretical approach, see: (d) Cossio, F. P.; Arrieta, A.; Lecea, B.; Ugalde, J. M. J. Am. Chem. Soc. 1994, 116, 2085-2093.
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21. 8. Compound 5 was prepared in one single step (64 % yield) from N-N-di-(p-methoxyphenyl) diimine and 4-pentynoyl chloride following our previously reported method. See: Alcaide, B.; Martín-Cantalejo, Y.; Pérez-Castells, J.; Rodríguez-López, J.; Sierra, M. A.; Monge, A.; Pérez-García, V. J. Org. Chem. 1992, 57, 5921-5931.
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24. 6 complexes 6 may be isolated and characterized if needed.
25. 11. Some examples on the use of TMANO to promote the P-K reaction: (a) Clive, D. L. J.; Cole, D. C.; Tao, Y. J. Org. Chem. 1994, 59, 1396-1406.
26. (b) Chung, Y. K.; Lee, B. Y.; Jeong, N.; Hudecek, M.; Pauson, P. L. Organometallics 1993, 12, 220-223.
27. 6 complexes in different reaction conditions included the standard conditions used in the P-K reaction. See, for example: (a) Rao, M. L. N.; Preiasamy, M. Organometallics 1996, 15, 442-445.
28. (b) Chisato, M.; Masahiko, U.; Miyoji, H. J. Chem. Soc., Chem. Commun. 1992, 1014-1015.
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35. 17. Strictly speaking, the possibility to obtain seven membered rings is not totally discarded since a propargyl group attached to the lactam nitrogen is present in compound 1a.
36. 6-alkyne complex was cooled to 0 °C and solid anhydrous TMANO (0.04 g, 0.5 mmol) was added. The reaction flask was open to the air and was warmed to room temperature by immediate removal of the ice bath. After 30 m, the reaction was again cooled to 0 °C, and 0.04 g (0.5 mmol) of solid anhydrous TMANO was added, and the solution was warmed again to room temperature by immediate removal of the ice bath. This sequence was repeated until a total of 3 mmol (0.24 g) of TMANO anh. was added. After that the solution was stirred for 1h at room temperature. During this period a purple precipitate was formed. TLC analysis indicated the complete disappearance of the starting material and the formation of a more polar, UV active spot. The crude mixture was diluted with EtOAc (20 mL) and filtrated through a short path of Celite. The solvent was removed under vacuum and a colorless solid was obtained. Crystallization (EtOAc/hexane) yields 0.11 g (80%) of compound 2b as colorless crystalline solid. Mp 159-160°C.
37. 19. For some selected references on the stereoselective Pauson-Khand reaction using enantiomerically pure reagents see, among others: (a) Verdaguer, X.; Moyano, A.; Pericàs, M. A.; Riera, A. J. Am. Chem. Soc. 1994, 116, 2153-2154.
38. (b) Castro, J.; Sörensen, H.; Riera, A.; Morin, C.; Moyano, A.; Pericàs, M. A.; Greene, A. E. J. Am. Chem. Soc. 1990, 112, 9388-9389.
39. (c) Park, J. J.: Lee, B. Y.: Kang, Y. K.; Chung, Y. K. Organometallics 1995, 14, 3104-3107.
40. (d) Hay, A. M.; Kerr, W. J.; Kirk, G. G.; Middlemiss, D. Organometallics 1995, 14, 4986-4988.