Synthesis of a Mexican bean beetle azamacrolide allomone via a novel lactam to lactone ring expansion

Tetrahedron Letters

Volumn 37, Issue 13, 1996, Pages 2145-2148

  Gribble, Gordon W ^a   Silva, Richard A ^a  

^a Dartmouth College ^*  (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; LACTONE DERIVATIVE; MACROCYCLIC COMPOUND;

ARTICLE; CONTROLLED STUDY; DRUG STRUCTURE; DRUG SYNTHESIS; INSECT CONTROL; NONHUMAN; REACTION ANALYSIS;

EID: 0029916431     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00234-1     Document Type: Article

References (27)

1. Attygalle, A.B.; McCormick, K.D.; Blankespoor, C.L.; Eisner, T.; Meinwald, J. Proc. Natl. Acad. Sci. USA 1993, 90, 5204. The biosynthesis of epilachnene (2) has also been studied: Attygalle, A.B.; Blankespoor, C.L.; Eisner, T.; Meinwald, J. Proc. Natl. Acad. Sci. USA 1994, 97, 12790.
2. Attygalle, A.B.; McCormick, K.D.; Blankespoor, C.L.; Eisner, T.; Meinwald, J. Proc. Natl. Acad. Sci. USA 1993, 90, 5204. The biosynthesis of epilachnene (2) has also been studied: Attygalle, A.B.; Blankespoor, C.L.; Eisner, T.; Meinwald, J. Proc. Natl. Acad. Sci. USA 1994, 97, 12790.
3. Rao, B.V.; Kumar, V.S. Tetrahedron Lett. 1995, 36, 147.
4. Inanaga, J.; Hirata, K.; Saeki, H.; Katsuki, T.; Yamaguchi, M. Bull. Chem. Soc. Jpn. 1979, 52, 1989.
5. Rao, A.V.R.; Rao, B.V.; Bhanu, M.N.; Kumar, V.S. Tetrahedron Lett. 1994, 35, 3201.
6. Meinwald, J. private communication. See accompanying Letter. We thank Professor Meinwald for communicating his results to us and for agreeing to joint publication.
7. Subsequent to the completion of most of this work, we became aware of a related ring expansion of N-hydroxyalkyl-2-piperidones under different conditions and requiring several steps: Yoshifuji, S.; Tanaka, K.; Arata, Y. Tetrahedron Lett. 1979, 809.
8. Corey, E.J.; Brunelle, D.J.; Nicolaou, K.C. J. Am. Chem. Soc. 1977, 99, 7359.
9. (a) Kramer, U.; Guggisberg, A.; Hesse, M.; Schmid, H. Helv. Chim. Acta 1978, 61, 1342.
10. (b) Song, J.; Hesse, M. Tetrahedron 1993, 49, 6797.
11. (c) Koch, T.; Hesse, M. Synthesis 1995, 251.
12. (d) Crombie, L.; Haigh, D.; Jones, R.C.F.; Mat-Zin, A.R. J. Chem. Soc., Perkin Trans. 1 1993, 2055.
13. (a) For a review of ring expansion reactions giving medium-sized rings, see Roxburgh, C.J. Tetrahedron 1993, 49, 10749.
14. (b) For a review of the synthesis of large rings, see Roxburgh, C.J. Tetrahedron 1995, 51, 9767.
15. (a) Mock, W.L.; Hartman, M.E. J. Am. Chem. Soc. 1970, 92, 5767.
16. (b) Mock, W.L.; Hartman, M.E. J. Org. Chem. 1977, 42, 459.
17. (c) Mock, W.L.; Hartman, M.E. J. Org. Chem. 1977, 42, 466.
18. (d) For a recent application of this excellent ring expansion method, see Boivin, J.; Huppé, S.; Zard, S.Z. Tetrahedron Lett. 1995, 36, 5737.
19. 3: 254.1882. Found: 254.1881.
20. Elsinger, F. Org. Syn. Coll. Vol. V 1973, 76.
21. 1: 183.1754. Found: 183.1748.
22. Olah, G.A.; Fung, A.P. Synthesis 1979, 537. For an independent discovery of this method, see Reddy, R.P.; Reddy, V.R.N.; Ravindranath, A.; Ramaiah, T.S. Ind. J. Chem. 1989, 28B, 850.
23. Olah, G.A.; Fung, A.P. Synthesis 1979, 537. For an independent discovery of this method, see Reddy, R.P.; Reddy, V.R.N.; Ravindranath, A.; Ramaiah, T.S. Ind. J. Chem. 1989, 28B, 850.
24. 1: C, 73.04; H, 11.75; N, 7.10. Found: C, 72.85, H, 11.63; N, 7.06.
25. 1: 237.2093. Found: 237.2092.
26. 2: 241.2044. Found: 241.2041.
27. +), 226, 199, 198 (100), 170, 142, 116, 99, 97, 72, 55.