An expedient one-pot synthesis for protected 2-thia-5-azabicyclo[2.2.1]heptan-3-ones. Versatile intermediates in the synthesis of carbapenem sidechains

Tetrahedron Letters

Volumn 37, Issue 17, 1996, Pages 2919-2922

  Brands, K M J ^a   Marchesini, G ^a   Williams, J M ^a   Dolling, U H ^a   Reider, P J ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

THIA;

CARBAPENEM DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0030007322     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00447-9     Document Type: Article

References (15)

1. a) Ratcliffe, R.W.; Albers-Schönberg, G. Chemistry and Biology of β-Lactam Antobiotics; Morin, R.B. and Gorman, M. (Eds.); Academic, 1982; Vol. 2; 227-313;
2. b) Salzman, T.N.; DiNinno, F.P.; Greenlee, M.L.; Guthikonda, R.N.; Quesada, M.L.; Schmitt, S.M.; Herrman, J.J.; Woods, M.F. in Recent Advances in the Chemistry and Biology of β-Lactam Antibiotics; Bentley, P.H. and Southgate, J.J. (Eds.); Royal Society of Chemistry: London, 1989; Special Publication No.70; 171-189.
3. Sunagawa, M.; Matsumura, H.; Inoue, T.; Fukasawa, M; Kato, M. J. Antibiot. 1990, 43, 519-532.
4. Matsumura, H.; Bando, T.; Sunagawa, M. Heterocycles 1995, 41, 147-159.
5. Three early reports on the synthesis of 2-thia-5-azabicyclo[2.2.1]heptan-3-ones are: a) Yamada, S.; Murakami, Y.; Koga, K. Tetrahedron Lett. 1968, 1501-1506;
6. b) Murakami, Y.; Koga, K.; Matsuo, H., Yamada, S. Chem. Pharm. Bull. 1972, 20, 543-549;
7. Verbiscar, A.J.; Witkop, B. J. Org. Chem. 1970, 35, 1924-1927.
8. Keller, O.; Keller, W.E.; van Look, G.; Wersin, G. Org. Synth. Coll. Vol. VII, 1993, 70-75.
9. We speculate that under these conditions the sulfonating agent is a methylsulfonyl pyridinium species which is presumed to be a more stable reagent than the corresponding sulfene (cf. Opitz, G.; Ehlis, T.; Rieth, K. Chem. Ber. 1990, 123, 1989-98).
10. Steliou, K; Salama, P.; Corriveau, J. J. Org. Chem. 1985, 50, 4969-4971.
11. iBu) in THF led only to low yields of 10.
12. Bodanszky, M. Principles of Peptide Synthesis; Springer: Heidelberg, 1993; 2nd Edition; 9-55.
13. 4 30/70 (0 min) to 60/40 (30 min) gradient (flowrate 1.0 mL/min); detection at 210 nm. The retention time for 10 under these conditions is 14.2 min.
14. For a recent detailed discussion of the application of carboxylic sulfonic mixed anhydrides see: Wirth, D.D. Tetrahedron 1993, 49, 1535-1540.
15. 2, -20°C; 100 MHz) δ 29.9/30.0 (q), 43.3/43.9 (t), 49.9/50.6 (d), 54.3/54.7 (t), 65.3/66.1 (d), 82.5/82.6 (s), 155.5/155.7 (s), 201.1/201.6 (s).