3,5-Bis(trifluoromethyl)phenyl sulfones in the modified Julia olefination: Application to the synthesis of resveratrol

Tetrahedron Letters

Volumn 45, Issue 3, 2004, Pages 573-577

  Alonso, Diego A ^a   Nájera, Carmen ^a   Varea, Montserrat ^a  

^a UNIVERSITY OF ALICANTE   (Spain)

Author keywords

(Z E) Selectivity; Julia olefination; Resveratrol; Sulfones

Indexed keywords

ALDEHYDE; ALKENE; POTASSIUM DERIVATIVE; STILBENE; STILBENE DERIVATIVE; SULFONE DERIVATIVE; TRIMETHOXYRESVERATROL; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; DRUG SYNTHESIS; JULIA KOCIENSKI REACTION; OLEFINATION; ROOM TEMPERATURE; STEREOCHEMISTRY; TEMPERATURE DEPENDENCE;

DRYAS IULIA;

EID: 0345732573     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.10.196     Document Type: Article

References (41)

1. (a) Wittig G., Geissler G. Justus Liebigs Ann. Chem. 580:1953;44-68
2. (b) Maryanoff B.E., Reitz A.B. Chem. Rev. 89:1989;863-927.
3. (a) Horner L., Hoffmann H., Wipel H.C., Klahre G. Chem. Ber. 92:1959;2499-2505
4. (b) Clayden J., Warren S. Angew. Chem., Int. Ed. Engl. 35:1996;241-270.
5. (a) Wadsworth W.S. Jr., Emmons W.D. J. Am. Chem. Soc. 83:1961;1733-1738
6. (b) Boutagy J., Thomas R. Chem. Rev. 74:1974;87-89.
7. (a) Peterson D.J. J. Org. Chem. 33:1968;780-784
8. (b) van Staden L.F., Gravestock D., Ager D.J. Chem. Soc. Rev. 31:2002;195-200.
9. Johnson C.R., Shanklin J.R., Kirchhoff R.A. J. Am. Chem. Soc. 95:1973;6462-6463.
10. Julia M., Paris J.-M. Tetrahedron Lett. 14:1973;4833-4836.
11. For a review about desulfonylation reactions, see: Nájera C., Yus M. Tetrahedron. 55:1999;10547-10658.
12. Prilezhaeva E.N. Russ. Chem. Rev. 69:2000;367-408.
13. (a) Baudin J.B., Hareau G., Julia S.A., Ruel O. Tetrahedron Lett. 32:1991;1175-1178
14. (b) Baudin J.B., Hareau G., Julia S.A., Lorne R., Ruel O. Bull. Soc. Chim. Fr. 130:1993;856-878
15. (c) Blakemore P.R. J. Chem. Soc., Perkin Trans. 1. 2002;2563-2585.
16. Charette A.B., Berthelette C., St-Martin D. Tetrahedron Lett. 42:2001;5149-5153. Corrigendum: Charette A.B., Berthelette C., St-Martin D. Tetrahedron Lett. 42:2001;6619.
17. Charette A.B., Berthelette C., St-Martin D. Tetrahedron Lett. 42:2001;5149-5153. Corrigendum: Charette A.B., Berthelette C., St-Martin D. Tetrahedron Lett. 42:2001;6619.
18. Blakemore P.R., Cole W.J., Kocienski P.J., Morley A. Synlett. 1998;26-28.
19. Kocienski P.J., Bell A., Blakemore P.R. Synlett. 2000;365-366.
20. (a) Alonso D.A., Nájera C., Varea M. Tetrahedron Lett. 42:2001;8845-8848
21. (b) Alonso D.A., Nájera C., Varea M. Helv. Chim. Acta. 85:2003;4287-4305.
22. Alonso D.A., Nájera C., Varea M. Synthesis. 2003;277-287.
23. Truce W.E., Kreider E.M., Brand W.W. Org. React. 18:1970;99-215.
24. This is a simple and general method for the oxidation of sulfides to sulfones: Alonso D.A., Nájera C., Varea M. Tetrahedron Lett. 43:2002;3459-3461.
25. (a) Schwesinger R. Paquette L.A. Encyclopedia of Reagents for Organic Synthesis. Vol. 6:1995;4110 Wiley, Chichester
26. (b) Schwesinger R., Schlemper H., Hasenfratz C., Willaredt J., Dambacher T., Breuer T., Ottaway C., Fletschinger M., Boele J., Fritz H., Putzas D., Rotter H.W., Bordwell F.G., Satish A.V., Ji G.-Z., Peters E.M., Peters K., von Schnering H.G., Walz L. Liebigs Ann. 1996;1055-1081
27. (c) Seebach D., Beck A.K., Studer A. Modern Synth. Meth. 7:1995;1-178.
28. Benzyl sulfones have been successfully deprotonated by phosphazene base P4-t-Bu in the diastereoselective aldol reaction with aldehydes: (a) Benzyl sulfones have been successfully deprotonated by phosphazene base P4-t-Bu in the diastereoselective aldol reaction with aldehydes: Solladié-Cavallo A., Roche D., Fischer J., De Chian A. J. Org. Chem. 61:1996;2690-2694 (b) Costa A., Nájera C., Sansano J.M. J. Org. Chem. 67:2002;5216-5225.
29. Benzyl sulfones have been successfully deprotonated by phosphazene base P4-t-Bu in the diastereoselective aldol reaction with aldehydes: (a) Benzyl sulfones have been successfully deprotonated by phosphazene base P4-t-Bu in the diastereoselective aldol reaction with aldehydes: Solladié-Cavallo A., Roche D., Fischer J., De Chian A. J. Org. Chem. 61:1996;2690-2694 (b) Costa A., Nájera C., Sansano J.M. J. Org. Chem. 67:2002;5216-5225.
30. Baudin J.B., Hareau G., Julia S.A., Ruel O. Bull. Soc. Chim. Fr. 130:1993;336-357.
31. Resveratrol, a natural polyhydroxylated stilbene, has been shown to exhibit a variety of unique and useful biological antioxidant, antimutagenic and lifespan extention properties: (a) Resveratrol, a natural polyhydroxylated stilbene, has been shown to exhibit a variety of unique and useful biological antioxidant, antimutagenic and lifespan extention properties: Siemann E.H., Creasy L.L. Am. J. Enol. Vitic. 43:1992;49-52 (b) Soleas G.J., Diamandis E.P., Goldberg D.M. Clin. Biochem. 62:1997;4821-4826 (c) Jang M., Cai L., Udenai G.O., Slowing K.V., Thomas C.F., Beecher C.W.W., Fong H.H.S., Farnsworth N.R., Kinghorn A.D., Mehta R.G., Moon R.C., Pezzuto J.M. Science. 275:1997;218-220 (d) Orsini F., Pelizzoni F., Verotta L., Aburjai T., Rogers C.B. J. Nat. Prod. 60:1997;1082-1087 (e) Fremont L. Life Sci. 66:2000;663-673 (f) Gusman J., Malonne H., Atassi G. Carcinogenesis. 22:2001;1111-1117 (g) Howitz K.T., Bitterman K.J., Cohen H.Y., Lamming D.W., Lavu S., Wood J.G., Zipkin R.E., Chung P., Kisielewski A., Zhang L.L., Scherer B., Sinclair D.A. Nature. 425:2003;191-196.
32. Resveratrol, a natural polyhydroxylated stilbene, has been shown to exhibit a variety of unique and useful biological antioxidant, antimutagenic and lifespan extention properties: (a) Resveratrol, a natural polyhydroxylated stilbene, has been shown to exhibit a variety of unique and useful biological antioxidant, antimutagenic and lifespan extention properties: Siemann E.H., Creasy L.L. Am. J. Enol. Vitic. 43:1992;49-52 (b) Soleas G.J., Diamandis E.P., Goldberg D.M. Clin. Biochem. 62:1997;4821-4826 (c) Jang M., Cai L., Udenai G.O., Slowing K.V., Thomas C.F., Beecher C.W.W., Fong H.H.S., Farnsworth N.R., Kinghorn A.D., Mehta R.G., Moon R.C., Pezzuto J.M. Science. 275:1997;218-220 (d) Orsini F., Pelizzoni F., Verotta L., Aburjai T., Rogers C.B. J. Nat. Prod. 60:1997;1082-1087 (e) Fremont L. Life Sci. 66:2000;663-673 (f) Gusman J., Malonne H., Atassi G. Carcinogenesis. 22:2001;1111-1117 (g) Howitz K.T., Bitterman K.J., Cohen H.Y., Lamming D.W., Lavu S., Wood J.G., Zipkin R.E., Chung P., Kisielewski A., Zhang L.L., Scherer B., Sinclair D.A. Nature. 425:2003;191-196.
33. Resveratrol, a natural polyhydroxylated stilbene, has been shown to exhibit a variety of unique and useful biological antioxidant, antimutagenic and lifespan extention properties: (a) Resveratrol, a natural polyhydroxylated stilbene, has been shown to exhibit a variety of unique and useful biological antioxidant, antimutagenic and lifespan extention properties: Siemann E.H., Creasy L.L. Am. J. Enol. Vitic. 43:1992;49-52 (b) Soleas G.J., Diamandis E.P., Goldberg D.M. Clin. Biochem. 62:1997;4821-4826 (c) Jang M., Cai L., Udenai G.O., Slowing K.V., Thomas C.F., Beecher C.W.W., Fong H.H.S., Farnsworth N.R., Kinghorn A.D., Mehta R.G., Moon R.C., Pezzuto J.M. Science. 275:1997;218-220 (d) Orsini F., Pelizzoni F., Verotta L., Aburjai T., Rogers C.B. J. Nat. Prod. 60:1997;1082-1087 (e) Fremont L. Life Sci. 66:2000;663-673 (f) Gusman J., Malonne H., Atassi G. Carcinogenesis. 22:2001;1111-1117 (g) Howitz K.T., Bitterman K.J., Cohen H.Y., Lamming D.W., Lavu S., Wood J.G., Zipkin R.E., Chung P., Kisielewski A., Zhang L.L., Scherer B., Sinclair D.A. Nature. 425:2003;191-196.
34. Resveratrol, a natural polyhydroxylated stilbene, has been shown to exhibit a variety of unique and useful biological antioxidant, antimutagenic and lifespan extention properties: (a) Resveratrol, a natural polyhydroxylated stilbene, has been shown to exhibit a variety of unique and useful biological antioxidant, antimutagenic and lifespan extention properties: Siemann E.H., Creasy L.L. Am. J. Enol. Vitic. 43:1992;49-52 (b) Soleas G.J., Diamandis E.P., Goldberg D.M. Clin. Biochem. 62:1997;4821-4826 (c) Jang M., Cai L., Udenai G.O., Slowing K.V., Thomas C.F., Beecher C.W.W., Fong H.H.S., Farnsworth N.R., Kinghorn A.D., Mehta R.G., Moon R.C., Pezzuto J.M. Science. 275:1997;218-220 (d) Orsini F., Pelizzoni F., Verotta L., Aburjai T., Rogers C.B. J. Nat. Prod. 60:1997;1082-1087 (e) Fremont L. Life Sci. 66:2000;663-673 (f) Gusman J., Malonne H., Atassi G. Carcinogenesis. 22:2001;1111-1117 (g) Howitz K.T., Bitterman K.J., Cohen H.Y., Lamming D.W., Lavu S., Wood J.G., Zipkin R.E., Chung P., Kisielewski A., Zhang L.L., Scherer B., Sinclair D.A. Nature. 425:2003;191-196.
35. Resveratrol, a natural polyhydroxylated stilbene, has been shown to exhibit a variety of unique and useful biological antioxidant, antimutagenic and lifespan extention properties: (a) Resveratrol, a natural polyhydroxylated stilbene, has been shown to exhibit a variety of unique and useful biological antioxidant, antimutagenic and lifespan extention properties: Siemann E.H., Creasy L.L. Am. J. Enol. Vitic. 43:1992;49-52 (b) Soleas G.J., Diamandis E.P., Goldberg D.M. Clin. Biochem. 62:1997;4821-4826 (c) Jang M., Cai L., Udenai G.O., Slowing K.V., Thomas C.F., Beecher C.W.W., Fong H.H.S., Farnsworth N.R., Kinghorn A.D., Mehta R.G., Moon R.C., Pezzuto J.M. Science. 275:1997;218-220 (d) Orsini F., Pelizzoni F., Verotta L., Aburjai T., Rogers C.B. J. Nat. Prod. 60:1997;1082-1087 (e) Fremont L. Life Sci. 66:2000;663-673 (f) Gusman J., Malonne H., Atassi G. Carcinogenesis. 22:2001;1111-1117 (g) Howitz K.T., Bitterman K.J., Cohen H.Y., Lamming D.W., Lavu S., Wood J.G., Zipkin R.E., Chung P., Kisielewski A., Zhang L.L., Scherer B., Sinclair D.A. Nature. 425:2003;191-196.
36. Resveratrol, a natural polyhydroxylated stilbene, has been shown to exhibit a variety of unique and useful biological antioxidant, antimutagenic and lifespan extention properties: (a) Resveratrol, a natural polyhydroxylated stilbene, has been shown to exhibit a variety of unique and useful biological antioxidant, antimutagenic and lifespan extention properties: Siemann E.H., Creasy L.L. Am. J. Enol. Vitic. 43:1992;49-52 (b) Soleas G.J., Diamandis E.P., Goldberg D.M. Clin. Biochem. 62:1997;4821-4826 (c) Jang M., Cai L., Udenai G.O., Slowing K.V., Thomas C.F., Beecher C.W.W., Fong H.H.S., Farnsworth N.R., Kinghorn A.D., Mehta R.G., Moon R.C., Pezzuto J.M. Science. 275:1997;218-220 (d) Orsini F., Pelizzoni F., Verotta L., Aburjai T., Rogers C.B. J. Nat. Prod. 60:1997;1082-1087 (e) Fremont L. Life Sci. 66:2000;663-673 (f) Gusman J., Malonne H., Atassi G. Carcinogenesis. 22:2001;1111-1117 (g) Howitz K.T., Bitterman K.J., Cohen H.Y., Lamming D.W., Lavu S., Wood J.G., Zipkin R.E., Chung P., Kisielewski A., Zhang L.L., Scherer B., Sinclair D.A. Nature. 425:2003;191-196.
37. Resveratrol, a natural polyhydroxylated stilbene, has been shown to exhibit a variety of unique and useful biological antioxidant, antimutagenic and lifespan extention properties: (a) Resveratrol, a natural polyhydroxylated stilbene, has been shown to exhibit a variety of unique and useful biological antioxidant, antimutagenic and lifespan extention properties: Siemann E.H., Creasy L.L. Am. J. Enol. Vitic. 43:1992;49-52 (b) Soleas G.J., Diamandis E.P., Goldberg D.M. Clin. Biochem. 62:1997;4821-4826 (c) Jang M., Cai L., Udenai G.O., Slowing K.V., Thomas C.F., Beecher C.W.W., Fong H.H.S., Farnsworth N.R., Kinghorn A.D., Mehta R.G., Moon R.C., Pezzuto J.M. Science. 275:1997;218-220 (d) Orsini F., Pelizzoni F., Verotta L., Aburjai T., Rogers C.B. J. Nat. Prod. 60:1997;1082-1087 (e) Fremont L. Life Sci. 66:2000;663-673 (f) Gusman J., Malonne H., Atassi G. Carcinogenesis. 22:2001;1111-1117 (g) Howitz K.T., Bitterman K.J., Cohen H.Y., Lamming D.W., Lavu S., Wood J.G., Zipkin R.E., Chung P., Kisielewski A., Zhang L.L., Scherer B., Sinclair D.A. Nature. 425:2003;191-196.
38. We believe that in this case, the presence of two electron-donating groups in sulfone 7b could prevent the diastereomeric equilibration through a retroaddition/addition process, due to the lower stability of the corresponding benzylic carbanion.
39. Other additives tested, such as DMPU, did not show any effect.
40. For a discussion about the nature of P4-t-Bu enolates, see: Fruchart J.-S., Gras-Masse H., Melnyk O. Tetrahedron Lett. 42:2001;9153-9155.
41. Compound 9f has been shown to be a potent and selective human cytochrome P450 1B1 inhibitor: Kim S., Ko H., Park J.E., Jung S., Lee S.K., Chun Y.-J. J. Med. Chem. 45:2002;160-164.