N-methoxy-N-acylnitrenium ions: Application to the formal synthesis of (±)-desmethylamino FR901483

Organic Letters

Volumn 3, Issue 15, 2001, Pages 2353-2356

  Wardrop, Duncan J ^a   Zhang, Wenming ^a  

^a UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BRIDGED COMPOUND; FR 901483; FUSED HETEROCYCLIC RINGS; HETEROCYCLIC COMPOUND; IMMUNOSUPPRESSIVE AGENT; ORGANOPHOSPHORUS COMPOUND; SPIRO COMPOUND;

ARTICLE; CHEMISTRY; SYNTHESIS;

AZA COMPOUNDS; BICYCLO COMPOUNDS, HETEROCYCLIC; BRIDGED COMPOUNDS; IMMUNOSUPPRESSIVE AGENTS; ORGANOPHOSPHORUS COMPOUNDS; SPIRO COMPOUNDS;

EID: 0035954860     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0161514     Document Type: Article

References (39)

1. Cyclosporin A; Borel, J. F., Ed.; Elsevier Biochemical Press: Amsterdam, 1982.
2. Schreiber, S. L. Cell 1992, 70, 365-368.
3. (a) Myers, B. D.; Ross, J.; Newton, L.; Leutscher, J.; Perlroth, M. N. Engl. J. Med. 1984, 311, 699-705.
4. (b) Shapiro, R.; Jordan, M.; Fung, J.; McCauley, J.; Johnston, J.; Iwaki, Y.; Tzakis, A.; Hakala, T.; Todo, S.; Starzl, T. E. Transplant Proc. 1991, 23, 920-923.
5. Sakamoto, K.; Tsujii, E.; Abe, F.; Nakanishi, T.; Yamashita, M.; Shigematsu, N.; Izumi, S.; Okuhara, M. J. Antibiot. 1996, 49, 37-44.
6. Although the mode of action of 1 remains to be elucidated, it has been suggested that FR901483 may interfere with the biosynthesis of purine: refs 3 and 6e.
7. (a) Snider, B. B.; Lin, H.; Foxman, B. M. J. Org. Chem. 1998, 63, 6442-6443.
8. (b) Snider, B. B.; Lin, H. J. Am. Chem. Soc. 1999, 121, 7778-7786.
9. (c) Scheffler, G.; Seike, H.; Sorensen, E. J. Angew. Chem., Int. Ed. 2000, 39, 4593-4596.
10. (d) Ousmer, M.; Braun, N. A.; Ciufolini, M. A. Org. Lett. 2001, 3, 765-767.
11. (e) Funk, R. L.; Maeng, J. H. Org. Lett. 2001, 3, 1125-1128.
12. (a) Yamazaki, N.; Suzuki, H.; Kibayashi, C. J. Org. Chem. 1997, 62, 8280-8281.
13. (b) Quirante, J.; Escolano, C.; Diaba, F.; Bonjoch, J. J. Chem. Soc., Perkin Trans. 1 1999, 1157-1162.
14. (c) Sole, D.; Peidro, E.; Bonjoch, J. Org. Lett. 2000, 2, 2225-2228.
15. (d) Suzuki, H.; Yamazaki, N.; Kibayashi, C. Tetrahedron Lett. 2001, 42, 3013-3015.
16. (e) Brummond, K.; Lu, J. Org. Lett. 2001, 3, 1347-1349.
17. Shirafuji, H.; Tsubotani, S.; Ishimaru, T.; Harada, S. PCT Int. Appl. WO 91 13,887,1991; Chem. Abstr. 1992, 116, 39780t.
18. Wardrop, D. J.; Basak, A. Org. Lett. 2001, 3, 1053-1056.
19. For a review of earlier synthetic studies on the 2-diazabicyclo[3.3.1]-nonane ring system, see: Bosch, J.; Bonjoch, J. Heterocycles 1980, 14, 505-529.
20. For a leading reference to the application of 6-exo-trig radical cyclizations in synthesis, see: Pedrosa, R.; Andrés, C.; Duque-Soladana, J. P.; Rosón, C. D. Tetrahedron: Asymmetry 2000, 11, 2809-2821 and references therein.
21. For reports of 6-exo-trig cyclizations involving the addition of radicals to the distal terminus of enol and thioether acceptors, see: (a) Marco-Contelles, J.; Sánchez, B. J. Org. Chem. 1993, 58, 4293-4297.
22. (b) Batty, D.; Crich, D.; Fortt, S. M. J. Chem. Soc., Chem. Commun. 1989, 1366-1368.
23. (c) Reference 7b.
24. The 6-endo-trig cyclization of alkenyl radicals with silyl enol ether acceptors has also been reported: Urabe, H.; Kuwajima, I. Tetrahedron Lett. 1986, 27, 1355-1358.
25. Stork, G.; Mook, R. J. Am. Chem. Soc. 1987, 109, 2829-2831.
26. While this work was in progress Bonjoch and co-workers reported a route to 2-azabicyclo[3.3.1]nonanes involving the 6-exo-trig cyclization of 1-(carbamoyl)dichloromethyl radicals with silyl enol ethers: ref 7b.
27. Davies, S. G.; Smyth, G. D. J. Chem. Soc., Perkin Trans. 1 1996, 2467-2477.
28. Knapp, S.; Gibson, F. S. J. Org. Chem. 1992, 57, 4802-4809.
29. Miller, R. D.; McKean, D. R. Synthesis 1979, 730-732.
30. This pyrrolizidine-based tricyclic ring system is present in the remarkable decacyclic alkaloid myrmicarin 663: Schröder, F.; Sinnwell, V.; Baumann, H.; Kaib, M.; Francke, W. Angew. Chem., Int. Ed. Engl. 1997, 36, 77-80.
31. Curran, D. P.; Porter, N. A.; Giese, B. Stereochemistry of Radical Reactions: Concepts, Guidelines and Synthetic Applications; VCH: Weinheim, 1996; pp 77-82.
32. (a) Lathbury, D. C.; Parsons, P. J.; Pinto, I. J. Chem. Soc., Chem. Commun. 1988, 81-82.
33. (b) For an informative review of the application of radical translocation-cyclization reactions in synthesis, see: Robertson, J.; Pillai, J.; Lush, R. K. Chem. Soc. Rev. 2001, 30, 94-103.
34. Huang, X. L.; Dannenberg, J. J. J. Org. Chem. 1991, 56, 5421-5424.
35. For a recent example of a 1,5-hydrogen atom transfer-cyclization process involving a vinyl stannane, see: Toyota, M.; Yokota, M.; Ihara, M. J. Am. Chem. Soc. 2001, 123, 1856-1861.
36. For a review of Lewis acid-mediated α-alkylations, see: Reetz, M. T. Angew. Chem., Int. Ed. Engl. 1982, 21, 96-108.
37. (a) Singh, A. K.; Bakshi, R. K.; Corey, E. J. J. Am. Chem. Soc. 1987, 109, 6187-6189.
38. (b) Molander, G. A. Org. React. 1994, 46 211-367.
39. For a report of the cleavage of a benzyl ether under similar conditions, see: Kutney, J. P.; Abdurahman, N.; Glestsos, C.; Le Quesne, P.; Piers, E.; Vlattas, I. J. Am. Chem. Soc. 1970, 92, 1727-1735.