Tandem oxyallylations and retro-ene eliminations. One pot stereoselective synthesis of polypropionate fragments with three contiguous stereogenic centers and one (E)-alkene unit

Tetrahedron Letters

Volumn 38, Issue 35, 1997, Pages 6201-6204

  Roulet, Jean Michel ^a,b   Puhr, Geneviève ^b   Vogel, Pierre ^b  

^a UNIVERSITÉ DE SHERBROOKE   (Canada)

^b UNIVERSITY OF LAUSANNE   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

DIMETHYL SULFONE; FUNCTIONAL GROUP; PROPIONIC ACID; SULFONE DERIVATIVE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030762386     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01398-1     Document Type: Article

References (27)

1. Deguin, B.; Roulet, J.-M.; Vogel, P. Tetrahedron Lett. preceding paper.
2. See e.g.: Wichterle, O.; Rocek, J. Chem. Listy 1953, 47, 1768; Kresze, G.; Maschpe, A.; Albrecht, R.; Bederke, K.; Patzschke, H.P.; Smalla, H.; Trede, A. Angew. Chem. 1982, 74, 135-144; Rogic, M. M.; Masilamani, D. J. Am. Chem. Soc. 1977, 99, 5219-5220; Braverman, S. in "The Chemistry of Sulfinic Acid, Esters and their Derivatives", Patai, S., Rappoport, Z.; Stirlind, C. J. M.; Eds., J. Wiley & Sons, Chichester, 1990, p. 298; Mock, W. L.; Nugent, R. M. J. Org. Chem. 1978, 43, 3433-3434; Garigipati, R. S.; Morton, J. A.; Weinreb, S. M. Tetrahedron Lett. 1983, 24, 987-990; Hiscock, S. D.; Isaacs, N. S.; King, M. D.; Young, D. J. J. Chem. Soc., Chem. Commun. 1994, 1381-1382; Corey, E. J.; Engler, T. A. Tetrahedron Lett. 1984, 25, 149-152; Baudin, J. B.; Julia, S. Bull. Soc. Chim. Fr. 1995, 132, 196-214.
3. See e.g.: Wichterle, O.; Rocek, J. Chem. Listy 1953, 47, 1768; Kresze, G.; Maschpe, A.; Albrecht, R.; Bederke, K.; Patzschke, H.P.; Smalla, H.; Trede, A. Angew. Chem. 1982, 74, 135-144; Rogic, M. M.; Masilamani, D. J. Am. Chem. Soc. 1977, 99, 5219-5220; Braverman, S. in "The Chemistry of Sulfinic Acid, Esters and their Derivatives", Patai, S., Rappoport, Z.; Stirlind, C. J. M.; Eds., J. Wiley & Sons, Chichester, 1990, p. 298; Mock, W. L.; Nugent, R. M. J. Org. Chem. 1978, 43, 3433-3434; Garigipati, R. S.; Morton, J. A.; Weinreb, S. M. Tetrahedron Lett. 1983, 24, 987-990; Hiscock, S. D.; Isaacs, N. S.; King, M. D.; Young, D. J. J. Chem. Soc., Chem. Commun. 1994, 1381-1382; Corey, E. J.; Engler, T. A. Tetrahedron Lett. 1984, 25, 149-152; Baudin, J. B.; Julia, S. Bull. Soc. Chim. Fr. 1995, 132, 196-214.
4. See e.g.: Wichterle, O.; Rocek, J. Chem. Listy 1953, 47, 1768; Kresze, G.; Maschpe, A.; Albrecht, R.; Bederke, K.; Patzschke, H.P.; Smalla, H.; Trede, A. Angew. Chem. 1982, 74, 135-144; Rogic, M. M.; Masilamani, D. J. Am. Chem. Soc. 1977, 99, 5219-5220; Braverman, S. in "The Chemistry of Sulfinic Acid, Esters and their Derivatives", Patai, S., Rappoport, Z.; Stirlind, C. J. M.; Eds., J. Wiley & Sons, Chichester, 1990, p. 298; Mock, W. L.; Nugent, R. M. J. Org. Chem. 1978, 43, 3433-3434; Garigipati, R. S.; Morton, J. A.; Weinreb, S. M. Tetrahedron Lett. 1983, 24, 987-990; Hiscock, S. D.; Isaacs, N. S.; King, M. D.; Young, D. J. J. Chem. Soc., Chem. Commun. 1994, 1381-1382; Corey, E. J.; Engler, T. A. Tetrahedron Lett. 1984, 25, 149-152; Baudin, J. B.; Julia, S. Bull. Soc. Chim. Fr. 1995, 132, 196-214.
5. See e.g.: Wichterle, O.; Rocek, J. Chem. Listy 1953, 47, 1768; Kresze, G.; Maschpe, A.; Albrecht, R.; Bederke, K.; Patzschke, H.P.; Smalla, H.; Trede, A. Angew. Chem. 1982, 74, 135-144; Rogic, M. M.; Masilamani, D. J. Am. Chem. Soc. 1977, 99, 5219-5220; Braverman, S. in "The Chemistry of Sulfinic Acid, Esters and their Derivatives", Patai, S., Rappoport, Z.; Stirlind, C. J. M.; Eds., J. Wiley & Sons, Chichester, 1990, p. 298; Mock, W. L.; Nugent, R. M. J. Org. Chem. 1978, 43, 3433-3434; Garigipati, R. S.; Morton, J. A.; Weinreb, S. M. Tetrahedron Lett. 1983, 24, 987-990; Hiscock, S. D.; Isaacs, N. S.; King, M. D.; Young, D. J. J. Chem. Soc., Chem. Commun. 1994, 1381-1382; Corey, E. J.; Engler, T. A. Tetrahedron Lett. 1984, 25, 149-152; Baudin, J. B.; Julia, S. Bull. Soc. Chim. Fr. 1995, 132, 196-214.
6. See e.g.: Wichterle, O.; Rocek, J. Chem. Listy 1953, 47, 1768; Kresze, G.; Maschpe, A.; Albrecht, R.; Bederke, K.; Patzschke, H.P.; Smalla, H.; Trede, A. Angew. Chem. 1982, 74, 135-144; Rogic, M. M.; Masilamani, D. J. Am. Chem. Soc. 1977, 99, 5219-5220; Braverman, S. in "The Chemistry of Sulfinic Acid, Esters and their Derivatives", Patai, S., Rappoport, Z.; Stirlind, C. J. M.; Eds., J. Wiley & Sons, Chichester, 1990, p. 298; Mock, W. L.; Nugent, R. M. J. Org. Chem. 1978, 43, 3433-3434; Garigipati, R. S.; Morton, J. A.; Weinreb, S. M. Tetrahedron Lett. 1983, 24, 987-990; Hiscock, S. D.; Isaacs, N. S.; King, M. D.; Young, D. J. J. Chem. Soc., Chem. Commun. 1994, 1381-1382; Corey, E. J.; Engler, T. A. Tetrahedron Lett. 1984, 25, 149-152; Baudin, J. B.; Julia, S. Bull. Soc. Chim. Fr. 1995, 132, 196-214.
7. See e.g.: Wichterle, O.; Rocek, J. Chem. Listy 1953, 47, 1768; Kresze, G.; Maschpe, A.; Albrecht, R.; Bederke, K.; Patzschke, H.P.; Smalla, H.; Trede, A. Angew. Chem. 1982, 74, 135-144; Rogic, M. M.; Masilamani, D. J. Am. Chem. Soc. 1977, 99, 5219-5220; Braverman, S. in "The Chemistry of Sulfinic Acid, Esters and their Derivatives", Patai, S., Rappoport, Z.; Stirlind, C. J. M.; Eds., J. Wiley & Sons, Chichester, 1990, p. 298; Mock, W. L.; Nugent, R. M. J. Org. Chem. 1978, 43, 3433-3434; Garigipati, R. S.; Morton, J. A.; Weinreb, S. M. Tetrahedron Lett. 1983, 24, 987-990; Hiscock, S. D.; Isaacs, N. S.; King, M. D.; Young, D. J. J. Chem. Soc., Chem. Commun. 1994, 1381-1382; Corey, E. J.; Engler, T. A. Tetrahedron Lett. 1984, 25, 149-152; Baudin, J. B.; Julia, S. Bull. Soc. Chim. Fr. 1995, 132, 196-214.
8. See e.g.: Wichterle, O.; Rocek, J. Chem. Listy 1953, 47, 1768; Kresze, G.; Maschpe, A.; Albrecht, R.; Bederke, K.; Patzschke, H.P.; Smalla, H.; Trede, A. Angew. Chem. 1982, 74, 135-144; Rogic, M. M.; Masilamani, D. J. Am. Chem. Soc. 1977, 99, 5219-5220; Braverman, S. in "The Chemistry of Sulfinic Acid, Esters and their Derivatives", Patai, S., Rappoport, Z.; Stirlind, C. J. M.; Eds., J. Wiley & Sons, Chichester, 1990, p. 298; Mock, W. L.; Nugent, R. M. J. Org. Chem. 1978, 43, 3433-3434; Garigipati, R. S.; Morton, J. A.; Weinreb, S. M. Tetrahedron Lett. 1983, 24, 987-990; Hiscock, S. D.; Isaacs, N. S.; King, M. D.; Young, D. J. J. Chem. Soc., Chem. Commun. 1994, 1381-1382; Corey, E. J.; Engler, T. A. Tetrahedron Lett. 1984, 25, 149-152; Baudin, J. B.; Julia, S. Bull. Soc. Chim. Fr. 1995, 132, 196-214.
9. See e.g.: Wichterle, O.; Rocek, J. Chem. Listy 1953, 47, 1768; Kresze, G.; Maschpe, A.; Albrecht, R.; Bederke, K.; Patzschke, H.P.; Smalla, H.; Trede, A. Angew. Chem. 1982, 74, 135-144; Rogic, M. M.; Masilamani, D. J. Am. Chem. Soc. 1977, 99, 5219-5220; Braverman, S. in "The Chemistry of Sulfinic Acid, Esters and their Derivatives", Patai, S., Rappoport, Z.; Stirlind, C. J. M.; Eds., J. Wiley & Sons, Chichester, 1990, p. 298; Mock, W. L.; Nugent, R. M. J. Org. Chem. 1978, 43, 3433-3434; Garigipati, R. S.; Morton, J. A.; Weinreb, S. M. Tetrahedron Lett. 1983, 24, 987-990; Hiscock, S. D.; Isaacs, N. S.; King, M. D.; Young, D. J. J. Chem. Soc., Chem. Commun. 1994, 1381-1382; Corey, E. J.; Engler, T. A. Tetrahedron Lett. 1984, 25, 149-152; Baudin, J. B.; Julia, S. Bull. Soc. Chim. Fr. 1995, 132, 196-214.
10. See e.g.: Wichterle, O.; Rocek, J. Chem. Listy 1953, 47, 1768; Kresze, G.; Maschpe, A.; Albrecht, R.; Bederke, K.; Patzschke, H.P.; Smalla, H.; Trede, A. Angew. Chem. 1982, 74, 135-144; Rogic, M. M.; Masilamani, D. J. Am. Chem. Soc. 1977, 99, 5219-5220; Braverman, S. in "The Chemistry of Sulfinic Acid, Esters and their Derivatives", Patai, S., Rappoport, Z.; Stirlind, C. J. M.; Eds., J. Wiley & Sons, Chichester, 1990, p. 298; Mock, W. L.; Nugent, R. M. J. Org. Chem. 1978, 43, 3433-3434; Garigipati, R. S.; Morton, J. A.; Weinreb, S. M. Tetrahedron Lett. 1983, 24, 987-990; Hiscock, S. D.; Isaacs, N. S.; King, M. D.; Young, D. J. J. Chem. Soc., Chem. Commun. 1994, 1381-1382; Corey, E. J.; Engler, T. A. Tetrahedron Lett. 1984, 25, 149-152; Baudin, J. B.; Julia, S. Bull. Soc. Chim. Fr. 1995, 132, 196-214.
11. Chain with alternating OH and Me substituents as they are found in a large number of natural products of biological interest, see e.g.: ref. 2 in : Kernen, P.; Vogel, P. Helv. Chim. Acta 1995, 78, 301-324; Vogel, P.; Sevin, A.-F.; Kernen, P.; Bialecki, M. Pure & Appl. Chem. 1996, 68, 719-722; Nocross, R. D.; Paterson, I. Chem. Rev. 1995, 95, 2041-2114; Marchionni, C.; Vogel, P.; Roversi, P. Tetrahedron Lett. 1996, 37, 4149-4152.
12. Chain with alternating OH and Me substituents as they are found in a large number of natural products of biological interest, see e.g.: ref. 2 in : Kernen, P.; Vogel, P. Helv. Chim. Acta 1995, 78, 301-324; Vogel, P.; Sevin, A.-F.; Kernen, P.; Bialecki, M. Pure & Appl. Chem. 1996, 68, 719-722; Nocross, R. D.; Paterson, I. Chem. Rev. 1995, 95, 2041-2114; Marchionni, C.; Vogel, P.; Roversi, P. Tetrahedron Lett. 1996, 37, 4149-4152.
13. Chain with alternating OH and Me substituents as they are found in a large number of natural products of biological interest, see e.g.: ref. 2 in : Kernen, P.; Vogel, P. Helv. Chim. Acta 1995, 78, 301-324; Vogel, P.; Sevin, A.-F.; Kernen, P.; Bialecki, M. Pure & Appl. Chem. 1996, 68, 719-722; Nocross, R. D.; Paterson, I. Chem. Rev. 1995, 95, 2041-2114; Marchionni, C.; Vogel, P.; Roversi, P. Tetrahedron Lett. 1996, 37, 4149-4152.
14. Chain with alternating OH and Me substituents as they are found in a large number of natural products of biological interest, see e.g.: ref. 2 in : Kernen, P.; Vogel, P. Helv. Chim. Acta 1995, 78, 301-324; Vogel, P.; Sevin, A.-F.; Kernen, P.; Bialecki, M. Pure & Appl. Chem. 1996, 68, 719-722; Nocross, R. D.; Paterson, I. Chem. Rev. 1995, 95, 2041-2114; Marchionni, C.; Vogel, P.; Roversi, P. Tetrahedron Lett. 1996, 37, 4149-4152.
15. Prepared from crotonaldehyde following a procedure similar to that described for 1-trimethylsilyloxybutadiene, see: Ishida, A.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1977, 50, 1161-1168.
16. Deguin, B.; Vogel, P. J. Am. Chem. Soc. 1992, 114, 9210-9211; Helv. Chim. Acta 1993, 76, 2250-2253.
17. Deguin, B.; Vogel, P. J. Am. Chem. Soc. 1992, 114, 9210-9211; Helv. Chim. Acta 1993, 76, 2250-2253.
18. Chen, K. M.; Gunderson, K. G.; Hardtmann, G. E.; Prasad, K.; Repic, O.; Shapiro, M. J. Chem. Lett. 1987, 1923-1930.
19. 3J=6.9, MeC(5)).
20. 3J(HC(4), HC(5))=2.6,3.1.
21. The structures of all the new compounds were confirmed with their spectral data and elemental analyses.
22. -3 Torr).
23. The structures of methylsulfones 23 have not been established unambigously. This will be done in a future full paper.
24. 3J=7.2).
25. 2 The relative configuration of the methyl group at C(1) of 28-31 is tentative. It has not been established unambigously.
26. Sevin, A.-F.; Vogel, P. J. Org. Chem. 1994, 59, 5920-5926.
27. 3J=7.5), 0.97 (s, 9H), 0.02 (s, 6H).