Stereoselective formation of tri- and tetracycles by samarium diiodide-induced cyclizations of naphthyl-substituted ketones

Organic Letters

Volumn 6, Issue 6, 2004, Pages 957-960

  Berndt, Mathias ^a   Hlobilová, Iva ^a   Reissig, Hans Ulrich ^a  

^a FREIE UNIVERSITÄT BERLIN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

KETONE DERIVATIVE; NAPHTHYL GROUP; SAMARIUM DIIODIDE; STEROID;

ANNULATION REACTION; ARTICLE; CHEMICAL BOND; CYCLIZATION; RING CLOSING METATHESIS; STEREOCHEMISTRY; SUBSTITUTION REACTION;

EID: 1642446516     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol036456d     Document Type: Article

References (48)

1. Girard, P.; Namy, J. L.; Kagan, H. B. J. Am. Chem. Soc. 1980, 102, 2693-2698.
2. Selected reviews on samarium diiodide-mediated reactions: (a) Kagan, H. B.; Namy, J. L. Tetrahedron 1986, 42, 6573-6614. (b) Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307-338. (c) Khan, F. A.; Zimmer, R. J. Prakt. Chem. 1997, 339, 101-104. (d) Molander, G. A.; Harris, C. R. Tetrahedron 1998, 54, 3321-3354. (e) Krief, A.; Laval, A.-M. Chem. Rev. 1999, 99, 745-777. (f) Kagan, H. B.; Namy, J. L. Top. Organomet. Chem. 1999, 2, 155-198. (g) Steel, P. G. J. Chem. Soc., Perkin Trans. 1 2001, 2727-2751. (h) Hölemann, A. Synlett 2001, 1497-1498. (i) Kagan, H. B. Tetrahedron 2003, 59, 10351-10372. (j) Berndt, M.; Gross, S.; Hölemann, A.; Reissig, H.-U. Synlett 2004, in press.
3. Selected reviews on samarium diiodide-mediated reactions: (a) Kagan, H. B.; Namy, J. L. Tetrahedron 1986, 42, 6573-6614. (b) Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307-338. (c) Khan, F. A.; Zimmer, R. J. Prakt. Chem. 1997, 339, 101-104. (d) Molander, G. A.; Harris, C. R. Tetrahedron 1998, 54, 3321-3354. (e) Krief, A.; Laval, A.-M. Chem. Rev. 1999, 99, 745-777. (f) Kagan, H. B.; Namy, J. L. Top. Organomet. Chem. 1999, 2, 155-198. (g) Steel, P. G. J. Chem. Soc., Perkin Trans. 1 2001, 2727-2751. (h) Hölemann, A. Synlett 2001, 1497-1498. (i) Kagan, H. B. Tetrahedron 2003, 59, 10351-10372. (j) Berndt, M.; Gross, S.; Hölemann, A.; Reissig, H.-U. Synlett 2004, in press.
4. Selected reviews on samarium diiodide-mediated reactions: (a) Kagan, H. B.; Namy, J. L. Tetrahedron 1986, 42, 6573-6614. (b) Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307-338. (c) Khan, F. A.; Zimmer, R. J. Prakt. Chem. 1997, 339, 101-104. (d) Molander, G. A.; Harris, C. R. Tetrahedron 1998, 54, 3321-3354. (e) Krief, A.; Laval, A.-M. Chem. Rev. 1999, 99, 745-777. (f) Kagan, H. B.; Namy, J. L. Top. Organomet. Chem. 1999, 2, 155-198. (g) Steel, P. G. J. Chem. Soc., Perkin Trans. 1 2001, 2727-2751. (h) Hölemann, A. Synlett 2001, 1497-1498. (i) Kagan, H. B. Tetrahedron 2003, 59, 10351-10372. (j) Berndt, M.; Gross, S.; Hölemann, A.; Reissig, H.-U. Synlett 2004, in press.
5. Selected reviews on samarium diiodide-mediated reactions: (a) Kagan, H. B.; Namy, J. L. Tetrahedron 1986, 42, 6573-6614. (b) Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307-338. (c) Khan, F. A.; Zimmer, R. J. Prakt. Chem. 1997, 339, 101-104. (d) Molander, G. A.; Harris, C. R. Tetrahedron 1998, 54, 3321-3354. (e) Krief, A.; Laval, A.-M. Chem. Rev. 1999, 99, 745-777. (f) Kagan, H. B.; Namy, J. L. Top. Organomet. Chem. 1999, 2, 155-198. (g) Steel, P. G. J. Chem. Soc., Perkin Trans. 1 2001, 2727-2751. (h) Hölemann, A. Synlett 2001, 1497-1498. (i) Kagan, H. B. Tetrahedron 2003, 59, 10351-10372. (j) Berndt, M.; Gross, S.; Hölemann, A.; Reissig, H.-U. Synlett 2004, in press.
6. Selected reviews on samarium diiodide-mediated reactions: (a) Kagan, H. B.; Namy, J. L. Tetrahedron 1986, 42, 6573-6614. (b) Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307-338. (c) Khan, F. A.; Zimmer, R. J. Prakt. Chem. 1997, 339, 101-104. (d) Molander, G. A.; Harris, C. R. Tetrahedron 1998, 54, 3321-3354. (e) Krief, A.; Laval, A.-M. Chem. Rev. 1999, 99, 745-777. (f) Kagan, H. B.; Namy, J. L. Top. Organomet. Chem. 1999, 2, 155-198. (g) Steel, P. G. J. Chem. Soc., Perkin Trans. 1 2001, 2727-2751. (h) Hölemann, A. Synlett 2001, 1497-1498. (i) Kagan, H. B. Tetrahedron 2003, 59, 10351-10372. (j) Berndt, M.; Gross, S.; Hölemann, A.; Reissig, H.-U. Synlett 2004, in press.
7. Selected reviews on samarium diiodide-mediated reactions: (a) Kagan, H. B.; Namy, J. L. Tetrahedron 1986, 42, 6573-6614. (b) Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307-338. (c) Khan, F. A.; Zimmer, R. J. Prakt. Chem. 1997, 339, 101-104. (d) Molander, G. A.; Harris, C. R. Tetrahedron 1998, 54, 3321-3354. (e) Krief, A.; Laval, A.-M. Chem. Rev. 1999, 99, 745-777. (f) Kagan, H. B.; Namy, J. L. Top. Organomet. Chem. 1999, 2, 155-198. (g) Steel, P. G. J. Chem. Soc., Perkin Trans. 1 2001, 2727-2751. (h) Hölemann, A. Synlett 2001, 1497-1498. (i) Kagan, H. B. Tetrahedron 2003, 59, 10351-10372. (j) Berndt, M.; Gross, S.; Hölemann, A.; Reissig, H.-U. Synlett 2004, in press.
8. Selected reviews on samarium diiodide-mediated reactions: (a) Kagan, H. B.; Namy, J. L. Tetrahedron 1986, 42, 6573-6614. (b) Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307-338. (c) Khan, F. A.; Zimmer, R. J. Prakt. Chem. 1997, 339, 101-104. (d) Molander, G. A.; Harris, C. R. Tetrahedron 1998, 54, 3321-3354. (e) Krief, A.; Laval, A.-M. Chem. Rev. 1999, 99, 745-777. (f) Kagan, H. B.; Namy, J. L. Top. Organomet. Chem. 1999, 2, 155-198. (g) Steel, P. G. J. Chem. Soc., Perkin Trans. 1 2001, 2727-2751. (h) Hölemann, A. Synlett 2001, 1497-1498. (i) Kagan, H. B. Tetrahedron 2003, 59, 10351-10372. (j) Berndt, M.; Gross, S.; Hölemann, A.; Reissig, H.-U. Synlett 2004, in press.
9. Selected reviews on samarium diiodide-mediated reactions: (a) Kagan, H. B.; Namy, J. L. Tetrahedron 1986, 42, 6573-6614. (b) Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307-338. (c) Khan, F. A.; Zimmer, R. J. Prakt. Chem. 1997, 339, 101-104. (d) Molander, G. A.; Harris, C. R. Tetrahedron 1998, 54, 3321-3354. (e) Krief, A.; Laval, A.-M. Chem. Rev. 1999, 99, 745-777. (f) Kagan, H. B.; Namy, J. L. Top. Organomet. Chem. 1999, 2, 155-198. (g) Steel, P. G. J. Chem. Soc., Perkin Trans. 1 2001, 2727-2751. (h) Hölemann, A. Synlett 2001, 1497-1498. (i) Kagan, H. B. Tetrahedron 2003, 59, 10351-10372. (j) Berndt, M.; Gross, S.; Hölemann, A.; Reissig, H.-U. Synlett 2004, in press.
10. Selected reviews on samarium diiodide-mediated reactions: (a) Kagan, H. B.; Namy, J. L. Tetrahedron 1986, 42, 6573-6614. (b) Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307-338. (c) Khan, F. A.; Zimmer, R. J. Prakt. Chem. 1997, 339, 101-104. (d) Molander, G. A.; Harris, C. R. Tetrahedron 1998, 54, 3321-3354. (e) Krief, A.; Laval, A.-M. Chem. Rev. 1999, 99, 745-777. (f) Kagan, H. B.; Namy, J. L. Top. Organomet. Chem. 1999, 2, 155-198. (g) Steel, P. G. J. Chem. Soc., Perkin Trans. 1 2001, 2727-2751. (h) Hölemann, A. Synlett 2001, 1497-1498. (i) Kagan, H. B. Tetrahedron 2003, 59, 10351-10372. (j) Berndt, M.; Gross, S.; Hölemann, A.; Reissig, H.-U. Synlett 2004, in press.
11. Selected reviews on samarium diiodide-mediated reactions: (a) Kagan, H. B.; Namy, J. L. Tetrahedron 1986, 42, 6573-6614. (b) Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307-338. (c) Khan, F. A.; Zimmer, R. J. Prakt. Chem. 1997, 339, 101-104. (d) Molander, G. A.; Harris, C. R. Tetrahedron 1998, 54, 3321-3354. (e) Krief, A.; Laval, A.-M. Chem. Rev. 1999, 99, 745-777. (f) Kagan, H. B.; Namy, J. L. Top. Organomet. Chem. 1999, 2, 155-198. (g) Steel, P. G. J. Chem. Soc., Perkin Trans. 1 2001, 2727-2751. (h) Hölemann, A. Synlett 2001, 1497-1498. (i) Kagan, H. B. Tetrahedron 2003, 59, 10351-10372. (j) Berndt, M.; Gross, S.; Hölemann, A.; Reissig, H.-U. Synlett 2004, in press.
12. (a) Molander, G. A.; Kenny, C. J. Am. Chem. Soc. 1989, 111, 8236-8246.
13. (b) Molander, G. A.; McKie, J. A. J. Org. Chem. 1992, 57, 3132-3139.
14. (c) Molander, G. A.; McKie, J. A. J. Org. Chem. 1994, 59, 3186-3192.
15. (d) Molander, G. A.; McKie, J. A. J. Org. Chem. 1995, 60, 872-882.
16. (a) Nandanan, E.; Dinesh, C. U.; Reissig, H.-U. Tetrahedron 2000, 56, 4267-4277.
17. (b) Hölemann, A. Ph.D. Dissertation 2004, Freie Universität Berlin.
18. (a) Dinesh, C. U.; Reissig, H.-U. Angew. Chem. 1999, 111, 874-876; Angew. Chem., Int. Ed. 1999, 38, 789-791.
19. (a) Dinesh, C. U.; Reissig, H.-U. Angew. Chem. 1999, 111, 874-876; Angew. Chem., Int. Ed. 1999, 38, 789-791.
20. (b) Berndt, M.; Reissig, H.-U. Synlett 2001, 1290-1292.
21. Related examples: (c) Schmalz, H.-G.; Siegel, S.; Bats, J. W. Angew. Chem. 1995, 107, 2597-2599; Angew. Chem. Int. Ed. 1995, 34, 2383-2385.
22. Related examples: (c) Schmalz, H.-G.; Siegel, S.; Bats, J. W. Angew. Chem. 1995, 107, 2597-2599; Angew. Chem. Int. Ed. 1995, 34, 2383-2385.
23. (d) Kuo, C.-W.; Fang, J. M. Synth. Commun. 2001, 31, 877-892.
24. (e) Ohno, H.; Wakayama, R.; Maeda, S.; Iwasaki, H.; Okumura, M.; Iwata, C.; Mikamiyama, H.; Tanaka, T. J. Org. Chem. 2003, 68, 5909-5916.
25. (f) Ohno, H.; Okumura, M.; Maeda, S.; Iwasaki, H.; Wakayama, R.; Tanaka, T. J. Org. Chem. 2003, 68, 7722-7732.
26. (a) Gross, S.; Reissig, H.-U. Synlett 2002, 2027-2030.
27. (b) Gross, S.; Reissig, H.-U. Org. Lett. 2003, 5, 4305-4307.
28. HMPA strongly raises the reducing power of samarium diiodide and is required for most ketyl coupling reactions. See: (a) Inanaga, J.; Ishikawa, M.; Yamaguchi, M. Chem. Lett. 1987, 1485-1486. (b) Prasad, E.; Flowers, R. A., II. J. Am. Chem. Soc. 2002, 124, 6895-6899.
29. HMPA strongly raises the reducing power of samarium diiodide and is required for most ketyl coupling reactions. See: (a) Inanaga, J.; Ishikawa, M.; Yamaguchi, M. Chem. Lett. 1987, 1485-1486. (b) Prasad, E.; Flowers, R. A., II. J. Am. Chem. Soc. 2002, 124, 6895-6899.
30. Compounds 7 and 9 were synthesized by Heck reaction of the corresponding bromonaphthalenes and 4-pentene-2-ol according to a known procedure: Taylor, E. C.; Wang, Y. Heterocycles 1998, 48, 1537-1553.
31. 2 substituent and the naphthalene ring in the transition structure. Generally, this group seems to prefer equatorial positions, when arene rings are the acceptor, however, the spatially extended naphthalene ring apparently changes this situation: (Equation Presented)
32. Ketone 11 was synthesized by alkylation of methyl 3-oxobutanoate with 1-bromomethylnaphthalene, followed by saponification and decarboxylation. Huckin, S. N.; Weiler, L. J. Am. Chem. Soc. 1974, 96, 1082-1087. Autorenkollektiv. Organikum, 18th ed.; Deutscher Verlag der Wissenschaften: Berlin, 1990; p 519.
33. Ketone 11 was synthesized by alkylation of methyl 3-oxobutanoate with 1-bromomethylnaphthalene, followed by saponification and decarboxylation. Huckin, S. N.; Weiler, L. J. Am. Chem. Soc. 1974, 96, 1082-1087. Autorenkollektiv. Organikum, 18th ed.; Deutscher Verlag der Wissenschaften: Berlin, 1990; p 519.
34. Compound 12 was already synthesized by cathodic reduction of the corresponding ketone 11: Kise, N.; Suzumoto, T.; Shono, T. J. Org. Chem. 1994, 59, 1407-1413.
35. Precursor 13 was prepared by the highly flexible sequence via siloxycyclopropanecarboxylates as published earlier; the alkylating agent in this case was 1-bromomethylnaphthalene: (a) Reichelt, I.; Reissig, H.-U. Liebigs Ann. Chem. 1984, 531-551. (b) Kunkel, E.; Reichelt, I.; Reissig, H.-U. Liebigs Ann. Chem. 1984, 802-819. (c) Khan, F. A.; Czerwonka, R.; H.-U. Reissig, Eur. J. Org. Chem. 2000, 3607-3617.
36. Precursor 13 was prepared by the highly flexible sequence via siloxycyclopropanecarboxylates as published earlier; the alkylating agent in this case was 1-bromomethylnaphthalene: (a) Reichelt, I.; Reissig, H.-U. Liebigs Ann. Chem. 1984, 531-551. (b) Kunkel, E.; Reichelt, I.; Reissig, H.-U. Liebigs Ann. Chem. 1984, 802-819. (c) Khan, F. A.; Czerwonka, R.; H.-U. Reissig, Eur. J. Org. Chem. 2000, 3607-3617.
37. Precursor 13 was prepared by the highly flexible sequence via siloxycyclopropanecarboxylates as published earlier; the alkylating agent in this case was 1-bromomethylnaphthalene: (a) Reichelt, I.; Reissig, H.-U. Liebigs Ann. Chem. 1984, 531-551. (b) Kunkel, E.; Reichelt, I.; Reissig, H.-U. Liebigs Ann. Chem. 1984, 802-819. (c) Khan, F. A.; Czerwonka, R.; H.-U. Reissig, Eur. J. Org. Chem. 2000, 3607-3617.
38. Berndt, M. Ph.D. Dissertation, Freie Universität Berlin, Berlin, 2003.
39. Similar lactonizations of related γ-hydroxy carboxylic esters are known: Khan, F. A.; Czerwonka, R.; Zimmer, R.; Reissig, H.-U. Synlett 1997, 995-997. See also ref 4a.
40. Berndt, M.; Brüdgam, I.; Hartl, H.; Reissig, H.-U. Z. Kristallogr. NCS 2004, submitted.
41. Compounds 16-20 were obtained by LDA-promoted alkylation of N-cyclohexyl imines of the corresponding cycloalkanones with 1-(2-iodoethyl)naphthalene as an electrophile. For analogous procedures, see: (a) Fleming, I.; Godhill, J. J. Chem. Soc., Perkin Trans. 1 1980, 1493-1498. (b) Fleming, I.; Godhill, J. J. Chem. Soc., Perkin Trans. 1 1982, 1563-1570. (c) Wallace, P.; Warren, S. J. Chem. Soc., Perkin Trans. 1 1992, 3169-3171.
42. Compounds 16-20 were obtained by LDA-promoted alkylation of N-cyclohexyl imines of the corresponding cycloalkanones with 1-(2-iodoethyl)naphthalene as an electrophile. For analogous procedures, see: (a) Fleming, I.; Godhill, J. J. Chem. Soc., Perkin Trans. 1 1980, 1493-1498. (b) Fleming, I.; Godhill, J. J. Chem. Soc., Perkin Trans. 1 1982, 1563-1570. (c) Wallace, P.; Warren, S. J. Chem. Soc., Perkin Trans. 1 1992, 3169-3171.
43. Compounds 16-20 were obtained by LDA-promoted alkylation of N-cyclohexyl imines of the corresponding cycloalkanones with 1-(2-iodoethyl)naphthalene as an electrophile. For analogous procedures, see: (a) Fleming, I.; Godhill, J. J. Chem. Soc., Perkin Trans. 1 1980, 1493-1498. (b) Fleming, I.; Godhill, J. J. Chem. Soc., Perkin Trans. 1 1982, 1563-1570. (c) Wallace, P.; Warren, S. J. Chem. Soc., Perkin Trans. 1 1992, 3169-3171.
44. Bonnaud, B.; Bigg, D. C. H. Synthesis 1994, 465-467.
45. Berndt, M.; Brüdgam, I.; Hartl, H.; Reissig, H.-U. Z. Kristallogr. NCS 2004, submitted.
46. 29, 31, 33, and 39 were synthesized starting from cyclopentanone or cyclohexanone as described in ref 12. Diastereomers 36 and 42 were prepared similarly with the corresponding ketal as a starting material.
47. 1H NMR signals.
48. Chair-like folding in the transition structure of 33 or 36 with the methoxycarbonyl group in an equatorial position would lead to compounds as depicted in Scheme 6; on the other hand, no comparable chair folding seems to operate for the reactions presented in Scheme 5.