Asymmetric acetate aldol reactions in connection with an enantioselective total synthesis of macrolactin A

Tetrahedron Letters

Volumn 37, Issue 49, 1996, Pages 8949-8952

  González, Ángel ^a   Aiguadé, Josep ^a   Urpí, Fèlix ^a   Vilarrasa, Jaume ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

MACROLACTIN A; MACROLIDE; UNCLASSIFIED DRUG;

ARTICLE; DIASTEREOISOMER; DRUG SYNTHESIS; ENANTIOMER; REACTION ANALYSIS;

EID: 0030566818     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02055-2     Document Type: Article

References (31)

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4. 2. Benvegnu, T.; Schio, L.; Le Floc'h, Y.; Grée, R. Synlett 1994, 505 (fragment C15-C24). Donaldson, W. A.; Bell, P. T.; Wang, Z.; Bennett, D. W. Tetrahedron Lett. 1994, 35, 5829 (fragments C1-C11 and C16-C24). Tanimori, S.; Morita, Y.; Tsubota, M.; Nakayama, M. Synth. Commun. 1996, 26, 559 (fragments C3-C9 and C17-C24).
5. 2. Benvegnu, T.; Schio, L.; Le Floc'h, Y.; Grée, R. Synlett 1994, 505 (fragment C15-C24). Donaldson, W. A.; Bell, P. T.; Wang, Z.; Bennett, D. W. Tetrahedron Lett. 1994, 35, 5829 (fragments C1-C11 and C16-C24). Tanimori, S.; Morita, Y.; Tsubota, M.; Nakayama, M. Synth. Commun. 1996, 26, 559 (fragments C3-C9 and C17-C24).
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7. 4. For recent reviews on stereoselective aldol-like reactions, see: Comprehensive Organic Synthesis, Vol. 2; Trost, B. M.; Fleming, I.; Eds.; Pergamon Press: Oxford, 1991 (Heathcock, C. H., p. 181; Kim, B. M.; Williams, S. F.; Masamune, S., p. 239; Paterson, I., p. 301; Gennari, C., p. 629). Mukaiyama, T.; Kobayashi, S. Org. React. 1994, 46, 1. Franklin, A. S.; Paterson, I. Contemp. Org. Synth. 1994, 1, 317. Bernardi, A.; Gennari, C.; Goodman, J. M.; Paterson, I. Tetrahedron: Asymmetry 1995, 6, 2613.
8. 4. For recent reviews on stereoselective aldol-like reactions, see: Comprehensive Organic Synthesis, Vol. 2; Trost, B. M.; Fleming, I.; Eds.; Pergamon Press: Oxford, 1991 (Heathcock, C. H., p. 181; Kim, B. M.; Williams, S. F.; Masamune, S., p. 239; Paterson, I., p. 301; Gennari, C., p. 629). Mukaiyama, T.; Kobayashi, S. Org. React. 1994, 46, 1. Franklin, A. S.; Paterson, I. Contemp. Org. Synth. 1994, 1, 317. Bernardi, A.; Gennari, C.; Goodman, J. M.; Paterson, I. Tetrahedron: Asymmetry 1995, 6, 2613.
9. 4. For recent reviews on stereoselective aldol-like reactions, see: Comprehensive Organic Synthesis, Vol. 2; Trost, B. M.; Fleming, I.; Eds.; Pergamon Press: Oxford, 1991 (Heathcock, C. H., p. 181; Kim, B. M.; Williams, S. F.; Masamune, S., p. 239; Paterson, I., p. 301; Gennari, C., p. 629). Mukaiyama, T.; Kobayashi, S. Org. React. 1994, 46, 1. Franklin, A. S.; Paterson, I. Contemp. Org. Synth. 1994, 1, 317. Bernardi, A.; Gennari, C.; Goodman, J. M.; Paterson, I. Tetrahedron: Asymmetry 1995, 6, 2613.
10. 4. For recent reviews on stereoselective aldol-like reactions, see: Comprehensive Organic Synthesis, Vol. 2; Trost, B. M.; Fleming, I.; Eds.; Pergamon Press: Oxford, 1991 (Heathcock, C. H., p. 181; Kim, B. M.; Williams, S. F.; Masamune, S., p. 239; Paterson, I., p. 301; Gennari, C., p. 629). Mukaiyama, T.; Kobayashi, S. Org. React. 1994, 46, 1. Franklin, A. S.; Paterson, I. Contemp. Org. Synth. 1994, 1, 317. Bernardi, A.; Gennari, C.; Goodman, J. M.; Paterson, I. Tetrahedron: Asymmetry 1995, 6, 2613.
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14. 7. For a recent review, see: Hughes, D. L. Org. React. 1992, 42, 335.
15. 8. Methyl (R)-lactate was also commercially available when we began this project, but it was/is too much expensive (in relation to the very cheap methyl and ethyl esters of L-lactic acid) to be used as a starting material. Isobutyl (R)-lactate is currently a relatively non-expensive substitute for methyl (R )-lactate.
16. 2 ; cf. Stowell, J. C.; Keith, D. R. Synthesis 1979, 132) and BuLi in THF, at -20 °C gave the corresponding alkene(s) in 82% yield.
17. 2 ; cf. Stowell, J. C.; Keith, D. R. Synthesis 1979, 132) and BuLi in THF, at -20 °C gave the corresponding alkene(s) in 82% yield.
18. 2 on Pd/C, is not recommended in this case, since the overall yields ranged only between 50% and 67% (the corresponding silanol being obtained as a co-product, probably owing to the allylic nature of the O-silyl substituent). For a related problem, see: Wattanasin, S.; Do, H. D.; Bhongle, N.; Kathawala, F. J. Org. Chem. 1993, 58, 1611.
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20. 11. Nagao, Y.; Hagiwara, Y.; Kumagai, T.; Ochiai, M.; Inoue, T.; Hashimoto, K.; Fujita, E. J. Org. Chem. 1986, 51, 2391. For very recent applications: Golec, J. M. C.; Jones, S. D. Tetrahedron Lett. 1993, 34, 8159. Sano, S.; Kobayashi, Y.; Kondo, T.; Takebayashi, M.; Maruyama, S.; Fujita, T.; Nagao, Y. Tetrahedron Lett. 1995, 36, 2097. For the preparation of oxazolidine-and thiazolidine-2-thiones, see: Delaunay, D.; Toupet, L.; Corre, M. L. J. Org. Chem. 1995, 60, 6604, and refs. 1-9 therein.
21. 11. Nagao, Y.; Hagiwara, Y.; Kumagai, T.; Ochiai, M.; Inoue, T.; Hashimoto, K.; Fujita, E. J. Org. Chem. 1986, 51, 2391. For very recent applications: Golec, J. M. C.; Jones, S. D. Tetrahedron Lett. 1993, 34, 8159. Sano, S.; Kobayashi, Y.; Kondo, T.; Takebayashi, M.; Maruyama, S.; Fujita, T.; Nagao, Y. Tetrahedron Lett. 1995, 36, 2097. For the preparation of oxazolidine-and thiazolidine-2-thiones, see: Delaunay, D.; Toupet, L.; Corre, M. L. J. Org. Chem. 1995, 60, 6604, and refs. 1-9 therein.
22. 11. Nagao, Y.; Hagiwara, Y.; Kumagai, T.; Ochiai, M.; Inoue, T.; Hashimoto, K.; Fujita, E. J. Org. Chem. 1986, 51, 2391. For very recent applications: Golec, J. M. C.; Jones, S. D. Tetrahedron Lett. 1993, 34, 8159. Sano, S.; Kobayashi, Y.; Kondo, T.; Takebayashi, M.; Maruyama, S.; Fujita, T.; Nagao, Y. Tetrahedron Lett. 1995, 36, 2097. For the preparation of oxazolidine-and thiazolidine-2-thiones, see: Delaunay, D.; Toupet, L.; Corre, M. L. J. Org. Chem. 1995, 60, 6604, and refs. 1-9 therein.
23. 12. Gennari, C.; Moresca, D.; Vieth, S.; Vulpetti, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 1618. For other applications, cf.: Gennari, C.; Pain, G.; Moresca, D. J. Org. Chem. 1995, 60, 6248.
24. 12. Gennari, C.; Moresca, D.; Vieth, S.; Vulpetti, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 1618. For other applications, cf.: Gennari, C.; Pain, G.; Moresca, D. J. Org. Chem. 1995, 60, 6248.
25. 13. Keck, G. E.; Krishnamurthy, D. J. Am. Chem. Soc. 1995, 117, 2363. For a related approach, using a more elaborate Ti-binaphthyl complex and silyl enolates of methyl acetate, with excellent results, see: Carreira, E. M.; Singer, R. A.; Lee, W. J. Am. Chem. Soc. 1994, 116, 8837.
26. 13. Keck, G. E.; Krishnamurthy, D. J. Am. Chem. Soc. 1995, 117, 2363. For a related approach, using a more elaborate Ti-binaphthyl complex and silyl enolates of methyl acetate, with excellent results, see: Carreira, E. M.; Singer, R. A.; Lee, W. J. Am. Chem. Soc. 1994, 116, 8837.
27. 2BCl, from (+)-α-pinene. For the use of Ipc enolates (of methyl ketones), see: Paterson, I. Pure & Appl. Chem. 1992, 64, 1821, and refs. therein. Ramachandran, P. V.; Xu, W., Brown, H. C. Tetrahedron Lett. 1996, 37, 4911, and refs. therein.
28. 2BCl, from (+)-α-pinene. For the use of Ipc enolates (of methyl ketones), see: Paterson, I. Pure & Appl. Chem. 1992, 64, 1821, and refs. therein. Ramachandran, P. V.; Xu, W., Brown, H. C. Tetrahedron Lett. 1996, 37, 4911, and refs. therein.
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30. 15. Mikami, K.; Matsukawa, S. J. Am. Chem. Soc. 1994, 116, 4078. Matsukawa, S.; Mikami, K. Tetrahedron: Asymmetry 1995, 6, 2571.
31. 16. In our case the aldehydes (dienals 3 and 4) are the most valuable materials.