Enantioselective Syntheses of Colletodiol, Colletol, and Grahamimycin A

Organic Letters

Volumn 4, Issue 25, 2002, Pages 4447-4450

  Hunter, Thomas J ^a,b   O'Doherty, George A ^a  

^a WEST VIRGINIA UNIVERSITY   (United States)

^b UNIVERSITY OF MINNESOTA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; COLLETODIOL; COLLETOL; GRAHAMIMYCIN A; LACTONE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; FUNGUS; SYNTHESIS;

ALCOHOLS; FUNGI; LACTONES; MOLECULAR STRUCTURE;

EID: 0037069707     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0269502     Document Type: Article

References (37)

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11. For the synthesis of colletodiol, see refs 5 and 8 and: (a) Tsutsui, H.; Mitsunobu, O. Tetrahedron Lett. 1984, 25, 2159-2162. (b) Tsutsui, H.; Mitsunobu, O. Tetrahedron Lett. 1984, 25, 263-2166. (c) Schnurrenberger, P.; Hungerbuhler, E.; Seebach, D. Liebigs Ann. Chem. 1987, 733-744. (d) Fujiji, M.; Omura, T.; Furuyama, M.-A. Shimizu, I. Tennen Yuki Kagobutsu Toronkai Koen Yoshishu 1997, 376-371.
12. For the synthesis of colletodiol, see refs 5 and 8 and: (a) Tsutsui, H.; Mitsunobu, O. Tetrahedron Lett. 1984, 25, 2159-2162. (b) Tsutsui, H.; Mitsunobu, O. Tetrahedron Lett. 1984, 25, 263-2166. (c) Schnurrenberger, P.; Hungerbuhler, E.; Seebach, D. Liebigs Ann. Chem. 1987, 733-744. (d) Fujiji, M.; Omura, T.; Furuyama, M.-A. Shimizu, I. Tennen Yuki Kagobutsu Toronkai Koen Yoshishu 1997, 376-371.
13. For the synthesis of colletodiol, see refs 5 and 8 and: (a) Tsutsui, H.; Mitsunobu, O. Tetrahedron Lett. 1984, 25, 2159-2162. (b) Tsutsui, H.; Mitsunobu, O. Tetrahedron Lett. 1984, 25, 263-2166. (c) Schnurrenberger, P.; Hungerbuhler, E.; Seebach, D. Liebigs Ann. Chem. 1987, 733-744. (d) Fujiji, M.; Omura, T.; Furuyama, M.-A. Shimizu, I. Tennen Yuki Kagobutsu Toronkai Koen Yoshishu 1997, 376-371.
14. For the synthesis of colletodiol, see refs 5 and 8 and: (a) Tsutsui, H.; Mitsunobu, O. Tetrahedron Lett. 1984, 25, 2159-2162. (b) Tsutsui, H.; Mitsunobu, O. Tetrahedron Lett. 1984, 25, 263-2166. (c) Schnurrenberger, P.; Hungerbuhler, E.; Seebach, D. Liebigs Ann. Chem. 1987, 733-744. (d) Fujiji, M.; Omura, T.; Furuyama, M.-A. Shimizu, I. Tennen Yuki Kagobutsu Toronkai Koen Yoshishu 1997, 376-371.
15. For the synthesis of colletol, see the work of Keck et al., ref 7, and: (a) Shimizu, I.; Omura, T. Chem. Lett. 1993, 1759-1760. (b) Sharma, G. V. M.; Raja Rao, A. V. S.; Murthy, V. S. Tetrahedron Lett. 1995, 36, 4117-4120. (c) Sallaoie, G.; Gressot, L. Colobert, F. Eur. J. Org. Chem. 2000, 357-364.
16. For the synthesis of colletol, see the work of Keck et al., ref 7, and: (a) Shimizu, I.; Omura, T. Chem. Lett. 1993, 1759-1760. (b) Sharma, G. V. M.; Raja Rao, A. V. S.; Murthy, V. S. Tetrahedron Lett. 1995, 36, 4117-4120. (c) Sallaoie, G.; Gressot, L. Colobert, F. Eur. J. Org. Chem. 2000, 357-364.
17. For the synthesis of colletol, see the work of Keck et al., ref 7, and: (a) Shimizu, I.; Omura, T. Chem. Lett. 1993, 1759-1760. (b) Sharma, G. V. M.; Raja Rao, A. V. S.; Murthy, V. S. Tetrahedron Lett. 1995, 36, 4117-4120. (c) Sallaoie, G.; Gressot, L. Colobert, F. Eur. J. Org. Chem. 2000, 357-364.
18. 1, see ref 6 and: (a) Ghiringhelli, D. Tetrahedron Lett. 1983, 24, 287-290. (b) Hillis, L. R.; Ronald, R. C. J. Org. Chem. 1985, 50, 470-473. (c) Bestmann, H.-J.; Miyagawa, O.; Tsutsui, H.; Mitsunobu, O. Bull. Chem. Soc. Jpn. 1993, 66, 523-535.
19. 1, see ref 6 and: (a) Ghiringhelli, D. Tetrahedron Lett. 1983, 24, 287-290. (b) Hillis, L. R.; Ronald, R. C. J. Org. Chem. 1985, 50, 470-473. (c) Bestmann, H.-J.; Miyagawa, O.; Tsutsui, H.; Mitsunobu, O. Bull. Chem. Soc. Jpn. 1993, 66, 523-535.
20. 1, see ref 6 and: (a) Ghiringhelli, D. Tetrahedron Lett. 1983, 24, 287-290. (b) Hillis, L. R.; Ronald, R. C. J. Org. Chem. 1985, 50, 470-473. (c) Bestmann, H.-J.; Miyagawa, O.; Tsutsui, H.; Mitsunobu, O. Bull. Chem. Soc. Jpn. 1993, 66, 523-535.
21. (a) Hunter, T. J.; O'Doherty, G. A. Org. Lett. 2001, 3, 1049-1052.
22. (b) Hunter, T. J.; O'Doherty, G. A. Org. Lett. 2001, 3, 2777-2780.
23. (c) Garaas, S.; Hunter, T. J.; O'Doherty, G. A. J. Org. Chem. 2002, 67, 2682-2685.
24. For a related but less efficient approach using the Sharpless epoxidation, see refs 9d and 10a.
25. The Aldrich Chemical Co. sells ethyl sorbate for $0.30/g.
26. All levels of enantioinduction were determined by HPLC analysis (8% IPA/Hexane, Chiralcel OD) and/or Mosher ester analysis. (a) Sullivan, G. R.; Dale, J. A.; Mosher, H. S. J. Org. Chem. 1973, 38, 2143. (b) Yamaguchi, S.; Yasuhara, F.; Kabuto, K. T. Tetrahedron 1976, 32, 1363.
27. All levels of enantioinduction were determined by HPLC analysis (8% IPA/Hexane, Chiralcel OD) and/or Mosher ester analysis. (a) Sullivan, G. R.; Dale, J. A.; Mosher, H. S. J. Org. Chem. 1973, 38, 2143. (b) Yamaguchi, S.; Yasuhara, F.; Kabuto, K. T. Tetrahedron 1976, 32, 1363.
28. 13C NMR, FTIR and HRMS.
29. (a) Tsuji, J.; Minami, I. Acc. Chem. Res. 1987, 20, 140.
30. (b) Hughes, G.; Lautens, M.; Wen, C. Org. Lett. 2000, 2, 107-110.
31. This lower than normal (2/1 phosphine to palladium) ratio gave higher yields and faster reaction times, whereas the use of ligandless conditions lead to the hydrogenation of the C-C double bond.
32. Sharpless has shown that the AD-mix reagent dihydroxylates simple dienoates and trienoates with good enantio- and diastereocontrol; see: (a) Xu, D.; Crispino, G. A.; Sharpless, K. B. J. Am. Chem. Soc. 1992, 114, 7570-7571. (b) Becker, H.; Soler, M. A.; Sharpless, K. B. Tetrahedron 1995, 51, 1345-76.
33. Sharpless has shown that the AD-mix reagent dihydroxylates simple dienoates and trienoates with good enantio- and diastereocontrol; see: (a) Xu, D.; Crispino, G. A.; Sharpless, K. B. J. Am. Chem. Soc. 1992, 114, 7570-7571. (b) Becker, H.; Soler, M. A.; Sharpless, K. B. Tetrahedron 1995, 51, 1345-76.
34. An interesting aspect of this reaction is that the stereochemical configuration, as well as, the electron withdrawing nature of the 6-hydroxy group of 14 protect the dienoate against further oxidation to a tetraol. This is evident from the observation that once the 6-hydroxyl group of 14 was removed (as in 16) the substrate readily oxidizes (16 to 17) under the AD-mix conditions.
35. This mixture could be used in the next step without separation of the double-bond isomers because the trans/cis diene isomer of 16 dihydroxylates at a much slower rate, see ref 23.
36. 3 can help prevent base-catalyzed side reactions; see: Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483-2547.
37. Diol 19 was isolated in a 71% yield along with ∼10% of the regioisomeric diol product and ∼5% of the recovered trans/cis diene isomer of 16.