Total synthesis of the proposed structure of lepadiformine via intramolecular N-acylnitroso Diels-Alder reaction

Tetrahedron Letters

Volumn 41, Issue 8, 2000, Pages 1205-1208

  Abe, Hideki ^a   Aoyagi, Sakae ^a   Kibayashi, Chihiro ^a  

^a TOKYO UNIVERSITY OF PHARMACY AND LIFE SCIENCES   (Japan)

Author keywords

Alkaloids; Cycloaddition; Cytotoxines; Nitroso compounds

Indexed keywords

ALKALOID DERIVATIVE; LEPADIFORMINE; NITROSO DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CONTROLLED STUDY; DRUG STRUCTURE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 0034685209     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)02172-3     Document Type: Article

References (21)

1. Biard, J. F.; Guyot, S.; Roussakis, C.; Verbist, J. F.; Vercauteren, J.; Weber, J. F.; Boukef, K. Tetrahedron Lett. 1994, 35, 2691-2694.
2. (a) Blackman, A. J.; Li, C.; Hockless, D. C. R.; Skelton, B. W.; White, A. H. Tetrahedron 1993, 38, 8645-8656.
3. (b) Li, C.; Blackman, A. J. Aust. J. Chem. 1994, 47, 1355-1361.
4. (c) Li, C.; Blackman, A. J. Aust. J. Chem. 1995, 48, 955-965.
5. (a) Pearson, W. H.; Barta, N. S.; Kampf, J. W. Tetrahedron Lett. 1997, 38, 3369-3372.
6. (b) Snider, B. B.; Liu, T. J. Org. Chem. 1997, 62, 5630-5633.
7. (c) Molander, G. A.; Rönn, M. J. Org. Chem. 1999, 64, 5183-5187.
8. For our own achievements in the development of the intramolecular acylnitroso-Diels-Alder approach for the synthesis of nitrogen-containing natural products, see: Kibayashi, C.; Aoyagi, S. Synlett 1995, 873-879.
9. For reviews on acylnitroso-Diels-Alder reaction, see: (a) Kirby, G. W. Chem. Soc. Rev. 1977, 6, 1-24. (b) Boger, D. L.; Weinreb, S. M. Hetero Diels-Alder Methodology in Organic Synthesis; Academic Press: San Diego, 1987. (c) Streith, J.; Defoin, A. Synthesis 1994, 1107-1117. (d) Orena, M. In Methods of Organic Chemistry (Houben-Weyl), 4th ed.; Helmchen, G.; Hoffmann, R. W.; Mulzer, J.; Schaumann, E., Eds.; Thieme: Stuttgart, 1995; Vol. E21e, pp. 5547-5587.
10. For reviews on acylnitroso-Diels-Alder reaction, see: (a) Kirby, G. W. Chem. Soc. Rev. 1977, 6, 1-24. (b) Boger, D. L.; Weinreb, S. M. Hetero Diels-Alder Methodology in Organic Synthesis; Academic Press: San Diego, 1987. (c) Streith, J.; Defoin, A. Synthesis 1994, 1107-1117. (d) Orena, M. In Methods of Organic Chemistry (Houben-Weyl), 4th ed.; Helmchen, G.; Hoffmann, R. W.; Mulzer, J.; Schaumann, E., Eds.; Thieme: Stuttgart, 1995; Vol. E21e, pp. 5547-5587.
11. For reviews on acylnitroso-Diels-Alder reaction, see: (a) Kirby, G. W. Chem. Soc. Rev. 1977, 6, 1-24. (b) Boger, D. L.; Weinreb, S. M. Hetero Diels-Alder Methodology in Organic Synthesis; Academic Press: San Diego, 1987. (c) Streith, J.; Defoin, A. Synthesis 1994, 1107-1117. (d) Orena, M. In Methods of Organic Chemistry (Houben-Weyl), 4th ed.; Helmchen, G.; Hoffmann, R. W.; Mulzer, J.; Schaumann, E., Eds.; Thieme: Stuttgart, 1995; Vol. E21e, pp. 5547-5587.
12. For reviews on acylnitroso-Diels-Alder reaction, see: (a) Kirby, G. W. Chem. Soc. Rev. 1977, 6, 1-24. (b) Boger, D. L.; Weinreb, S. M. Hetero Diels-Alder Methodology in Organic Synthesis; Academic Press: San Diego, 1987. (c) Streith, J.; Defoin, A. Synthesis 1994, 1107-1117. (d) Orena, M. In Methods of Organic Chemistry (Houben-Weyl), 4th ed.; Helmchen, G.; Hoffmann, R. W.; Mulzer, J.; Schaumann, E., Eds.; Thieme: Stuttgart, 1995; Vol. E21e, pp. 5547-5587.
13. (a) Kirby, G. W.; Sweeny, J. G. J. Chem. Soc., Chem. Commun. 1973, 704-705.
14. (b) Corrie, J. E. T.; Kirby, G. W.; Sharma, R. P. J. Chem. Soc., Chem. Commun. 1975, 915-916.
15. (c) Keck, G. Tetrahedron Lett. 1978, 4767-4770.
16. When the cycloaddition was performed using the hydroxamic acid lacking a bromine atom, the preferential formation of the B/C trans-fused adduct via an anti-facial transition state was observed (unpublished result).
17. Myers, A. G.; Yang, B. H.; Kopecky, D. J. Tetrahedron Lett. 1996, 37, 3623-3626.
18. The stereostructure of 28 was verified by NOE study.
19. (a) Werner, K. M.; de los Santos, J, M.; Weinreb, S. M.; Shang, M. J. Org. Chem. 1999, 64, 686-687.
20. (b) Werner, K. M.; de los Santos, J. M.; Weinreb, S. M.; Shang, M. J. Org. Chem. 1999, 64, 4865-4873.
21. Pearson, W. H.; Ren, Y. J. Org. Chem. 1999, 64, 688-689.