The remarkable effect of cosolvent on a samarium(II)-mediated 4-exo-trig cyclization: Further synthetic studies on pestalotiopsin A

Journal of Organic Chemistry

Volumn 68, Issue 8, 2003, Pages 3190-3198

  Edmonds, David J ^a   Muir, Kenneth W ^a   Procter, David J ^a  

^a UNIVERSITY OF GLASGOW   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

COSOLVENTS; CYCLIDATION REACTIONS;

ALDEHYDES; ETHERS; SAMARIUM; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

ORGANIC SOLVENTS;

ALDEHYDE; COORDINATION COMPOUND; ETHER DERIVATIVE; FUNCTIONAL GROUP; PESTALOTIOPSIN A; SAMARIUM; SESQUITERPENE; SOLVENT; TERT BUTYL DIMETHYLSILYL ETHER; TRIFLUOROETHANOL; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; STEREOCHEMISTRY; SYNTHESIS;

CYCLIZATION; INDICATORS AND REAGENTS; LACTONES; MOLECULAR STRUCTURE; SAMARIUM; SESQUITERPENES; SOLVENTS; STEREOISOMERISM;

EID: 0037453621     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo026827o     Document Type: Article

References (29)

1. For reviews on the use of samarium(II) iodide in organic synthesis, see: (a) Soderquist, J. A. Aldrichim. Acta 1991, 24, 15. (b) Molander, G. A. Chem. Rev. 1992, 92, 29-68. (c) Molander, G. A. Org. React. 1994, 46, 211. (d) Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307. (e) Molander, G. A.; Harris, C. R. Tetrahedron 1998, 54, 3321. (f) Krief, A.; Laval, A.-M. Chem. Rev. 1999, 99, 745. (g) Steel, P. G. J. Chem. Soc., Perkin Trans. 1 2001, 2727.
2. For reviews on the use of samarium(II) iodide in organic synthesis, see: (a) Soderquist, J. A. Aldrichim. Acta 1991, 24, 15. (b) Molander, G. A. Chem. Rev. 1992, 92, 29-68. (c) Molander, G. A. Org. React. 1994, 46, 211. (d) Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307. (e) Molander, G. A.; Harris, C. R. Tetrahedron 1998, 54, 3321. (f) Krief, A.; Laval, A.-M. Chem. Rev. 1999, 99, 745. (g) Steel, P. G. J. Chem. Soc., Perkin Trans. 1 2001, 2727.
3. For reviews on the use of samarium(II) iodide in organic synthesis, see: (a) Soderquist, J. A. Aldrichim. Acta 1991, 24, 15. (b) Molander, G. A. Chem. Rev. 1992, 92, 29-68. (c) Molander, G. A. Org. React. 1994, 46, 211. (d) Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307. (e) Molander, G. A.; Harris, C. R. Tetrahedron 1998, 54, 3321. (f) Krief, A.; Laval, A.-M. Chem. Rev. 1999, 99, 745. (g) Steel, P. G. J. Chem. Soc., Perkin Trans. 1 2001, 2727.
4. For reviews on the use of samarium(II) iodide in organic synthesis, see: (a) Soderquist, J. A. Aldrichim. Acta 1991, 24, 15. (b) Molander, G. A. Chem. Rev. 1992, 92, 29-68. (c) Molander, G. A. Org. React. 1994, 46, 211. (d) Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307. (e) Molander, G. A.; Harris, C. R. Tetrahedron 1998, 54, 3321. (f) Krief, A.; Laval, A.-M. Chem. Rev. 1999, 99, 745. (g) Steel, P. G. J. Chem. Soc., Perkin Trans. 1 2001, 2727.
5. For reviews on the use of samarium(II) iodide in organic synthesis, see: (a) Soderquist, J. A. Aldrichim. Acta 1991, 24, 15. (b) Molander, G. A. Chem. Rev. 1992, 92, 29-68. (c) Molander, G. A. Org. React. 1994, 46, 211. (d) Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307. (e) Molander, G. A.; Harris, C. R. Tetrahedron 1998, 54, 3321. (f) Krief, A.; Laval, A.-M. Chem. Rev. 1999, 99, 745. (g) Steel, P. G. J. Chem. Soc., Perkin Trans. 1 2001, 2727.
6. For reviews on the use of samarium(II) iodide in organic synthesis, see: (a) Soderquist, J. A. Aldrichim. Acta 1991, 24, 15. (b) Molander, G. A. Chem. Rev. 1992, 92, 29-68. (c) Molander, G. A. Org. React. 1994, 46, 211. (d) Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307. (e) Molander, G. A.; Harris, C. R. Tetrahedron 1998, 54, 3321. (f) Krief, A.; Laval, A.-M. Chem. Rev. 1999, 99, 745. (g) Steel, P. G. J. Chem. Soc., Perkin Trans. 1 2001, 2727.
7. For reviews on the use of samarium(II) iodide in organic synthesis, see: (a) Soderquist, J. A. Aldrichim. Acta 1991, 24, 15. (b) Molander, G. A. Chem. Rev. 1992, 92, 29-68. (c) Molander, G. A. Org. React. 1994, 46, 211. (d) Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307. (e) Molander, G. A.; Harris, C. R. Tetrahedron 1998, 54, 3321. (f) Krief, A.; Laval, A.-M. Chem. Rev. 1999, 99, 745. (g) Steel, P. G. J. Chem. Soc., Perkin Trans. 1 2001, 2727.
8. (a) Johnston, D.; McCusker, C. M.; Procter, D. J. Tetrahedron Lett. 1999, 40, 4913.
9. (b) Johnston, D.; McCusker, C. F.; Muir, K.; Procter, D. J. J. Chem. Soc., Perkin Trans. 1 2000, 681.
10. Prior to our work, a single example of such a cyclization had been described by Weinges: Weinges, K.; Schmidbauer, S. B.; Schick, H. Chem. Ber. 1994, 127, 1305.
11. Johnston, D.; Francon, N.; Edmonds, D. J.; Procter, D. J. Org. Lett. 2001, 3, 2001.
12. (a) Pulici, M.; Sugawara, F.; Koshino, H.; Uzawa, J.; Yoshida, S.; Lobkovsky, E.; Clardy, J. J. Org. Chem. 1996, 61, 2122.
13. (b) Pulici, M.; Sugawara, F.; Koshino, H.; Okada, G.; Esumi, Y.; Uzawa, J.; Yoshida, S. Phytochemistry 1997, 46, 313.
14. Kende has reported a synthetic intermediate having a related structure in his approach to Punctaporin B. See ref 13a.
15. 2-mediated transformations. Eight-membered chelates in particular have been invoked to rationalize stereoselectivity in a number of reactions; see: (a) Evans, D. A.; Hoveyda, A. H. J. Am. Chem. Soc. 1990, 112, 6447. (b) Molander, G. A.; Etter, J. B.; Harring, L. S.; Thorel, P.-J. J. Am. Chem. Soc. 1991, 113, 8036. (c) Molander, G. A.; McKie, J. A. J. Am. Chem. Soc. 1993, 115, 5821. (d) Keck, G. E.; Truong, A. P. Org. Lett. 2002, 4, 3131.
16. 2-mediated transformations. Eight-membered chelates in particular have been invoked to rationalize stereoselectivity in a number of reactions; see: (a) Evans, D. A.; Hoveyda, A. H. J. Am. Chem. Soc. 1990, 112, 6447. (b) Molander, G. A.; Etter, J. B.; Harring, L. S.; Thorel, P.-J. J. Am. Chem. Soc. 1991, 113, 8036. (c) Molander, G. A.; McKie, J. A. J. Am. Chem. Soc. 1993, 115, 5821. (d) Keck, G. E.; Truong, A. P. Org. Lett. 2002, 4, 3131.
17. 2-mediated transformations. Eight-membered chelates in particular have been invoked to rationalize stereoselectivity in a number of reactions; see: (a) Evans, D. A.; Hoveyda, A. H. J. Am. Chem. Soc. 1990, 112, 6447. (b) Molander, G. A.; Etter, J. B.; Harring, L. S.; Thorel, P.-J. J. Am. Chem. Soc. 1991, 113, 8036. (c) Molander, G. A.; McKie, J. A. J. Am. Chem. Soc. 1993, 115, 5821. (d) Keck, G. E.; Truong, A. P. Org. Lett. 2002, 4, 3131.
18. 2-mediated transformations. Eight-membered chelates in particular have been invoked to rationalize stereoselectivity in a number of reactions; see: (a) Evans, D. A.; Hoveyda, A. H. J. Am. Chem. Soc. 1990, 112, 6447. (b) Molander, G. A.; Etter, J. B.; Harring, L. S.; Thorel, P.-J. J. Am. Chem. Soc. 1991, 113, 8036. (c) Molander, G. A.; McKie, J. A. J. Am. Chem. Soc. 1993, 115, 5821. (d) Keck, G. E.; Truong, A. P. Org. Lett. 2002, 4, 3131.
19. Prestwich has shown that aldol reactions of the dianion derived from this lactone proceed with approach of the aldehyde from the opposite face to the ring alkoxide; see: Shieh, H.-M.; Prestwich, G. D. J. Org. Chem. 1981, 46, 4319.
20. See the Supporting Information for details of X-ray analyses of compounds 8b, 10, 13, epi-13, and 15.
21. For the role of an OTBDMS group in a samarium(II)-mediated reduction, see: Keck, G. E.; Wager, C. A. Org. Lett. 2000, 2, 2307.
22. 2-mediated transformations, leading to a loss of stereoselectivity. For an illustrative example, see: Fukazawa, S.-I.; Seki, K.; Tatsuzawa, M.; Mutoh, K. J. Am. Chem. Soc. 1997, 119, 1482.
23. Shabangi, M.; Flowers, R. A. Tetrahedron Lett. 1997, 38, 1137. (b) Shabangi, M.; Sealy, J. M.; Fuchs, J. R.; Flowers, R. A. Tetrahedron Lett. 1998, 39, 4429. (c) Enemaerke, R. J.; Hertz, T.; Skrydstrup, T.; Daasbjerg, K. Chem. Eur. J. 2000, 6, 3747. (d) Miller, R. S.; Sealy, J. M.; Shabangi, M.; Kuhlman, M. L.; Fuchs, J. R.; Flowers, R. A. J. Am. Chem. Soc. 2000, 122, 7718.
24. Shabangi, M.; Flowers, R. A. Tetrahedron Lett. 1997, 38, 1137. (b) Shabangi, M.; Sealy, J. M.; Fuchs, J. R.; Flowers, R. A. Tetrahedron Lett. 1998, 39, 4429. (c) Enemaerke, R. J.; Hertz, T.; Skrydstrup, T.; Daasbjerg, K. Chem. Eur. J. 2000, 6, 3747. (d) Miller, R. S.; Sealy, J. M.; Shabangi, M.; Kuhlman, M. L.; Fuchs, J. R.; Flowers, R. A. J. Am. Chem. Soc. 2000, 122, 7718.
25. Shabangi, M.; Flowers, R. A. Tetrahedron Lett. 1997, 38, 1137. (b) Shabangi, M.; Sealy, J. M.; Fuchs, J. R.; Flowers, R. A. Tetrahedron Lett. 1998, 39, 4429. (c) Enemaerke, R. J.; Hertz, T.; Skrydstrup, T.; Daasbjerg, K. Chem. Eur. J. 2000, 6, 3747. (d) Miller, R. S.; Sealy, J. M.; Shabangi, M.; Kuhlman, M. L.; Fuchs, J. R.; Flowers, R. A. J. Am. Chem. Soc. 2000, 122, 7718.
26. Shabangi, M.; Flowers, R. A. Tetrahedron Lett. 1997, 38, 1137. (b) Shabangi, M.; Sealy, J. M.; Fuchs, J. R.; Flowers, R. A. Tetrahedron Lett. 1998, 39, 4429. (c) Enemaerke, R. J.; Hertz, T.; Skrydstrup, T.; Daasbjerg, K. Chem. Eur. J. 2000, 6, 3747. (d) Miller, R. S.; Sealy, J. M.; Shabangi, M.; Kuhlman, M. L.; Fuchs, J. R.; Flowers, R. A. J. Am. Chem. Soc. 2000, 122, 7718.
27. For a similar addition/trans-lactonization sequence on a cyclobutanone substrate, see: (a) Kende, A. S.; Kaldor, I.; Aslanian, R. J. Am. Chem. Soc. 1988, 110, 6265. (b) Kende, A. S.; Kaldor, I. Tetrahedron Lett. 1989, 30, 7329.
28. For a similar addition/trans-lactonization sequence on a cyclobutanone substrate, see: (a) Kende, A. S.; Kaldor, I.; Aslanian, R. J. Am. Chem. Soc. 1988, 110, 6265. (b) Kende, A. S.; Kaldor, I. Tetrahedron Lett. 1989, 30, 7329.
29. Imamoto, T.; Ono, M. Chem. Lett. 1987, 501.