Ethynyloxirane anions: A new tool for natural product synthesis

Tetrahedron

Volumn 59, Issue 49, 2003, Pages 9793-9802

  Klein, Sophie ^a   Zhang, Jing H ^a   Holler, Michel ^a   Weibel, Jean Marc ^a   Pale, Patrick ^a  

^a CNRS   (France)

Author keywords

Deprotonation; Ethynyl oxiranes; Oxirane

Indexed keywords

ALDEHYDE DERIVATIVE; ANION; ETHYLENE OXIDE DERIVATIVE; IODINE DERIVATIVE; NATURAL PRODUCT;

ALKYLATION; ARTICLE; CHEMICAL REACTION; PRIORITY JOURNAL; PROTON TRANSPORT; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0242391302     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2003.10.012     Document Type: Article

References (61)

1. The term 'oxiranyl anions' or 'oxiranions' refered to organometallics derived from oxirane ring, regardless of their exact nature.
2. (a) Oxiranyl anions rearrange to α-alkoxy carbenes at very low temperature; see: Crandall J.K., Apparu M. Org. React. 29:1983;345. and references therein
3. (b)For other carbene like but controlled reactions from oxiranyl anions, see: Doris E., Dechaux L., Mioskowski C. Synlett. 1998;337-348.
4. Satoh T. Chem. Rev. 96:1996;3303-3325.
5. (a) Eisch J.J., Galle J.E. J. Am. Chem. Soc. 98:1976;4646-4648
6. (b) Eisch J.J., Galle J.E. J. Org. Chem. 41:1976;2615-261
7. (c) Eisch J.J., Galle J.E. J. Organomet. Chem. 121:1976;C10-C14
8. (d) Eisch J.J., Galle J.E. J. Organomet. Chem. 341:1988;293-313.
9. Burford C., Cooke F., Roy G., Magnus P. Tetrahedron. 39:1983;867-876.
10. (a) Molander G.A., Mautner K. J. Org. Chem. 54:1989;4042-4050
11. (b) Murthi K.K., Salomon R.G. Tetrahedron Lett. 35:1995;517-520
12. (c) Marié J.C., Courillon C., Malacria M. Synlett. 2002;553-555.
13. (a) Ashwell M., Jackson R.F. Chem. Commun. 1988;645
14. (b) Hewkin C.T., Jackson R.F.W., Clegg W. Tetrahedron Lett. 29:1988;4889
15. Hewkin C. T., Jackson R.F.W., Tetrahedron Lett. 1990:31;1877-1880
16. (d) Ashwell M., Clegg W., Jackson R.F.W. J. Chem. Soc., Perkin Trans. 1. 1991;897.
17. Yamauchi K., Katagiri T., Unemaya K. Org. Lett. 4:2002;173-176.
18. Florio S., Capriati V., Di Martino S., Abbotto A. Eur. J. Org. Chem. 2:1999;409-417.
19. Florio S., Ingrosso G., Troisi L., Lucchini V. Tetrahedron Lett. 34:1993;1363-1366.
20. (a) Eisch J.J., Galle J.E. J. Org. Chem. 55:1990;4835-4840
21. (b) Capriati V., Florio S., Luisi R., Salomone A. Org. Lett. 4:2002;2445-2448.
22. (a) Hodgson D.M., Norsikian L.M. Org. Lett. 3:2001;461-463
23. (b) Hodgson D.M., Gras E. Angew. Chem. Int. Ed. 41:2002;2376-2378.
24. Dubuffet T., Sauvêtre R., Normant J.F. Tetrahedron Lett. 29:1988;5923-5924.
25. Lohse P., Loner H., Acklin P., Sternfeld F., Pfalz A. Tetrahedron Lett. 32:1991;615-618.
26. (a) Satoh T., Horiguchi K. Tetrahedron Lett. 36:1995;8235-8238
27. (b) Satoh T., Kobayashi S., Horiguchi K., Irisa S. Tetrahedron. 55:1999;2515-2528.
28. Shimizu M., Fujimoto T., Minezaki H., Hata T., Hiyama T. J. Am. Chem. Soc. 123:2001;6947-6948.
29. A few examples nevertheless showed that even non-stabilized oxiranyl anions could be trapped by electrophiles; see Refs. 12,14-16.
30. (a) Mori Y., Yaegashi K., Furukawa H. Tetrahedron. 53:1997;12917-12932
31. (b) Mori Y., Yaegashi K. Pandalai S.G. Recent Research Developments in Organic Chemistry. Vol. 3:1999;207-217 Transworld Research Network, Trivandrum
32. (c) Kuramochi K., Itaya H., Nagata S., Takao K., Kobayashi S. Tetrahedron Lett. 40:1999;7367-7370. see also 7371-7374.
33. (a) Bohlmann F., Burkhardt T., Zdero C. Naturally Occurring Acetylenes. 1973;Academic, New York
34. (b) Bohlmann F., Rode K.M., Zdero C. Chem. Ber. 100:1967;537-541
35. (c) Bohlmann F., Jakupovic. J. Phytochem. 18:1979;131-133.
36. (a) Guerriero A., D'Ambroso M. Eur. J. Org. Chem. 2:1999;1985-1990
37. (b) Lemee R., Pesando D., Durand-Clément M., Dubreuil A., Meinesz A., Guerriero A., Pietra F. J. Appl. Phycol. 5:1993;485-493
38. (c) Guerriero A., Marchetti F., D'Ambroso M., Senesi S., Dini F., Pietra F. Helv. Chem. Acta. 76:1993;855-864.
39. (a) Okazaki T., Naito A. Sankyo Kenkyusho Nenpo. 38:1986;80-89. Jpn. Kokai Tokkyo Koho Appl. JP 82-231355, 1984
40. (b) Takahashi S., Itoh Y., Takeuchi M., Furuya K., Komada K., Naito A., Haneishi T., Sato S., Tamura C. J. Antibiot. 36:1983;1418-1420.
41. NCS: (a) Ishida N., Miyazaki K., Kumagai K.M., Rikimura M. J. Antibiot. 18:1965;68-76 (b) Edo K., Mizugaki M., Koide Y., Seto H., Furihata K., Otake N., Ishida N. Tetrahedron Lett. 26:1999;331-334. N1999A2: (c) Ando T., Ishii M., Kajiura T., Kameyama T., Miwa K., Sugiura Y. Tetrahedron Lett. 39:1998;6495-6498. Kedarcidin: (d) Hofstead S.J., Matson J.A., Malacko A.R., Marquard H. J. Antibiot. 45:1992;1250-1254 (e) Leet J.E., Schroeder D.R., Hofstead S.J., Golik J., Colson K.L., Huang S., Klohr S.E., Doyle T.W., Matson J.A. J. Am. Chem. Soc. 114:1992;7946-7948.
42. NCS: (a) Ishida N., Miyazaki K., Kumagai K.M., Rikimura M. J. Antibiot. 18:1965;68-76 (b) Edo K., Mizugaki M., Koide Y., Seto H., Furihata K., Otake N., Ishida N. Tetrahedron Lett. 26:1999;331-334. N1999A2: (c) Ando T., Ishii M., Kajiura T., Kameyama T., Miwa K., Sugiura Y. Tetrahedron Lett. 39:1998;6495-6498. Kedarcidin: (d) Hofstead S.J., Matson J.A., Malacko A.R., Marquard H. J. Antibiot. 45:1992;1250-1254 (e) Leet J.E., Schroeder D.R., Hofstead S.J., Golik J., Colson K.L., Huang S., Klohr S.E., Doyle T.W., Matson J.A. J. Am. Chem. Soc. 114:1992;7946-7948.
43. NCS: (a) Ishida N., Miyazaki K., Kumagai K.M., Rikimura M. J. Antibiot. 18:1965;68-76 (b) Edo K., Mizugaki M., Koide Y., Seto H., Furihata K., Otake N., Ishida N. Tetrahedron Lett. 26:1999;331-334. N1999A2: (c) Ando T., Ishii M., Kajiura T., Kameyama T., Miwa K., Sugiura Y. Tetrahedron Lett. 39:1998;6495-6498. Kedarcidin: (d) Hofstead S.J., Matson J.A., Malacko A.R., Marquard H. J. Antibiot. 45:1992;1250-1254 (e) Leet J.E., Schroeder D.R., Hofstead S.J., Golik J., Colson K.L., Huang S., Klohr S.E., Doyle T.W., Matson J.A. J. Am. Chem. Soc. 114:1992;7946-7948.
44. NCS: (a) Ishida N., Miyazaki K., Kumagai K.M., Rikimura M. J. Antibiot. 18:1965;68-76 (b) Edo K., Mizugaki M., Koide Y., Seto H., Furihata K., Otake N., Ishida N. Tetrahedron Lett. 26:1999;331-334. N1999A2: (c) Ando T., Ishii M., Kajiura T., Kameyama T., Miwa K., Sugiura Y. Tetrahedron Lett. 39:1998;6495-6498. Kedarcidin: (d) Hofstead S.J., Matson J.A., Malacko A.R., Marquard H. J. Antibiot. 45:1992;1250-1254 (e) Leet J.E., Schroeder D.R., Hofstead S.J., Golik J., Colson K.L., Huang S., Klohr S.E., Doyle T.W., Matson J.A. J. Am. Chem. Soc. 114:1992;7946-7948.
45. NCS: (a) Ishida N., Miyazaki K., Kumagai K.M., Rikimura M. J. Antibiot. 18:1965;68-76 (b) Edo K., Mizugaki M., Koide Y., Seto H., Furihata K., Otake N., Ishida N. Tetrahedron Lett. 26:1999;331-334. N1999A2: (c) Ando T., Ishii M., Kajiura T., Kameyama T., Miwa K., Sugiura Y. Tetrahedron Lett. 39:1998;6495-6498. Kedarcidin: (d) Hofstead S.J., Matson J.A., Malacko A.R., Marquard H. J. Antibiot. 45:1992;1250-1254 (e) Leet J.E., Schroeder D.R., Hofstead S.J., Golik J., Colson K.L., Huang S., Klohr S.E., Doyle T.W., Matson J.A. J. Am. Chem. Soc. 114:1992;7946-7948.
46. (a) Pale P., Chuche J. Tetrahedron Lett. 28:1987;6447
47. (b) Pale P., Chuche J. Tetrahedron Lett. 29:1988;2947
48. (c) Grandjean D., Pale P., Chuche J. Tetrahedron Lett. 32:1991;3043
49. (d) Chuche J., Grandjean D., Pale P. Bull. Soc. Chim. Belg. 101:1992;415
50. (e) Grandjean D., Pale P., Chuche J. Tetrahedron Lett. 33:1992;5355
51. (f) Grandjean D., Pale P., Chuche J. Tetrahedron Lett. 33:1992;4905
52. (g) Grandjean D., Pale P., Chuche J. Tetrahedron. 49:1993;5225
53. (h) Bertus P., Pale P. J. Organomet. Chem. 567:1998;173-180
54. (i) Pale P., Chuche J. Eur. J. Org. Chem. 2000;1019-1025.
55. (a) Finn M.G., Sharpless K.B. Morrison J.D. Asymmetric synthesis. Vol. 5:1985;247 Academic, New York
56. (a) Finn M.G., Sharpless K.B. Morrison J.D. Asymmetric synthesis. Vol. 5:1985;247 Academic, New York, (b) Grandjean D., Pale P., Chuche J. Tetrahedron Lett. 32:1991;3043.
57. A premiminary account of this work has been published: Grandjean D., Pale P., Chuche J. Tetrahedron: Asymmetry. 4:1993;1991.
58. Grandjean D., Pale P., Chuche J. Tetrahedron Lett. 35:1994;3529.
59. For 1,4-silyl migrations, see: Lautens M., Delanghe P.H.M., Goh J.B., Zhang C.H. J. Org. Chem. 5:1992;3270. and references therein.
60. Bassindale A.R., Ellis R.J., Lau J.C.Y., Taylor P.G. J. Chem. Soc., Chem. Commun. 1986;98-100.
61. Grandjean D., Pale P., Chuche J. Tetrahedron. 47:1991;1215.