Synthesis of (-)-9,10-epi-stemoamide

Journal of Organic Chemistry

Volumn 69, Issue 22, 2004, Pages 7734-7736

  Khim, Seock Kyu ^a   Schultz, Arthur G ^a  

^a Research Rensselaer Polytechnic Institute   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

LITHIUM COMPOUNDS; SYNTHESIS (CHEMICAL);

FRAGMENTATION REACTIONS; LITHIUM HYDROXIDES; RADICAL CYCLIZATION;

ORGANIC COMPOUNDS;

9,10 EPISTEMOAMIDE; ALKALOID DERIVATIVE; LITHIUM DERIVATIVE; LITHIUM HYDROXIDE; RADICAL; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CATALYST; CHEMICAL REACTION; CHIRALITY; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; FRAGMENTATION REACTION; REACTION ANALYSIS; REDUCTION; REPRODUCIBILITY; ROOM TEMPERATURE; TECHNIQUE;

ALKALOIDS; CATALYSIS; HETEROCYCLIC COMPOUNDS, 3-RING; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; PLANTS, MEDICINAL; STEMONACEAE; STEREOISOMERISM;

EID: 6344285667     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo049083i     Document Type: Article

References (33)

1. Lin, W.-H.; Ye, Y.; Xu, K.-S. J. Nat. Prod. 1992, 55, 571.
2. (a) Williams, D. R.; Reddy, J. P.; Amato, G. S. Tetrahedron Lett. 1994, 35, 6417.
3. (b) Kinoshita, A.; Mori, M. J. Org. Chem. 1996, 61, 8356.
4. (c) Kinoshita, A.; Mori, M. Heterocycles 1997, 46, 287.
5. (d) Kohno, Y.; Narasaka, K. Bull. Chem. Soc. Jpn. 1996, 69, 2063.
6. (e) Jacobi, P. A.; Lee, K. J. Am. Chem. Soc. 1997, 119, 3409.
7. (f) Jacobi, P. A.; Lee, K. J. Am. Chem. Soc. 2000, 122, 4295.
8. (g) Gurjar, M. K.; Keddy, D. S. Tetrahedron Lett. 2002, 43, 295.
9. For reviews of Birch reduction-alkylation methodologies and their synthetic applications, see: (a) Schultz, A. G. Acc. Chem. Res. 1990, 23, 207.
10. (b) Schultz, A. G. J. Chin. Chem. Soc. (Taipei) 1994, 41, 487.
11. (c) Schultz, A. G. Chem. Commun. 1999, 14, 1263.
12. (a) Schultz, A. G.; Dai, M.; Khim, S.-K.; Pettus, L.; Thakkar, K. Tetrahedron Lett. 1998, 39, 4203.
13. (b) Khim, S.-K.; Dai, M.; Zhang, X.; Lei, C.; Pettus, L.; Thakkar, K.; Schultz, A. G. J. Org. Chem. 2004, 69, 7728.
14. The enantiomeric excesses (ee %) of 7 and 8 were determined by chiral HPLC to be >99 and >96%, respectively.
15. Compound 7 could be obtained in a slightly better yield by taking a different route (two-step sequence): Schultz, A. G.; Zhang, X. Chem. Commun. 2000, 399.
16. Yoon, N. M.; Pak, C. S.; Brown, H. C.; Krishnamurthy, S.; Stocky, T. P. J. Org. Chem. 1973, 38, 2786.
17. (a) Mitsunobu, O. Synthesis 1981, 1.
18. (b) Hughes, D. L. Org. React. 1992, 42, 335.
19. (a) Chamberlin, A. R.; Nguyen, D. H.; Chung, J. Y. L. J. Org. Chem. 1984, 49, 1682.
20. (b) Hiemstra, H.; Speckamp, W. In Comprehensive Organic Synthesis', Heathcock, C. H., Ed.; Pergamon Press: Oxford, 1991; Vol. 2, p 1047.
21. For the preparation of phenylthiolactam and its use in radical cyclization reactions, see: Choi, J.-K.; Hart, D. J. Tetrahedron 1985, 41, 3959 and references therein.
22. For recent reviews of the radical cyclization reactions, see: (a) Curran, D. P. In Comprehensive Organic Synthesis; Semmelhack, M. F., Ed.; Pergamon Press: Oxford, 1991; Vol. 4, p 779.
23. (b) Renaud, P.; Giraud, L. Synthesis 1996, 913.
24. For a few examples of seven-membered ring formations by intramolecular radical cyclizations, see: (a) Beckwith, A. L. J.; Moad, G. J. Chem. Soc., Chem. Commun. 1974, 472.
25. (b) Beckwith, A. L. J.; Roberts, D. H. J. Am. Chem. Soc. 1986, 108, 5893.
26. (c) Bachi, M. D.; Hoornaert, C. Tetrahedron Lett. 1981, 22, 2693.
27. (d) Ghosh, A. K.; Ghosh, K.; Pal, S.; Ghatak, U. R. J. Chem. Soc., Chem. Commun. 1993, 809.
28. (e) Rigby, J. M.; Qabar, M. N. J. Org. Chem. 1993, 58, 4473.
29. (f) Rigby, J. M.; Laurent, S.; Cavezza, A.; Heeg, M. J. J. Org. Chem. 1998, 63, 5587.
30. 1H NMR analysis of the crude reaction mixture.
31. 13C NMR spectra of 2 were identical to those prepared by Jacobi and Lee (see ref 2e).
32. For general experimental procedures and full characterization data of 3-8, see ref 4b.
33. Curran, D. P.; Chang, C.-T. J. Org. Chem. 1989, 54, 3140.