'Naked sugars of the second generation': Asymmetric synthesis of long-chain polypropionates and analogues starting with acetone

Pure and Applied Chemistry

Volumn 68, Issue 3, 1996, Pages 719-722

  Vogel, Pierre ^a   Sevin, Anne Françoise ^a   Kernen, Philippe ^a   Bialecki, Maciej ^a  

^a UNIVERSITY OF LAUSANNE   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000571373     PISSN: 00334545     EISSN: None     Source Type: Journal    
DOI: 10.1351/pac199668030719     Document Type: Article

References (25)

1. See e.g. ref. 1, 2 of ref. 2.
2. A.-F. Sevin and P. Vogel. J.Org.Chem. 59, 5290 (1994).
3. a) R. Stürmer, K. Ritter and R.W. Hoffmann. Angew.Chem.Int.Ed.Engl. 32, 101 (1993). R.W. Hoffmann and R. Stürmer, Antibiotics and Antiviral Compounds, p. 103, K. Krohn, H.A. Kirst, H. Maag, Eds., VCH, Weinheim (1993).
4. a) R. Stürmer, K. Ritter and R.W. Hoffmann. Angew.Chem.Int.Ed.Engl. 32, 101 (1993). R.W. Hoffmann and R. Stürmer, Antibiotics and Antiviral Compounds, p. 103, K. Krohn, H.A. Kirst, H. Maag, Eds., VCH, Weinheim (1993).
5. For methods and strategies developed to prepare polypropionates, see e.g. ref. 3-22 of ref. 2.
6. G. Stork and S.D. Rychnovsky. J.Am.Chem.Soc. 109, 1565 (1987). See also: J. Mulzer, H.M. Kirstein, J. Buschmann, C. Lehmann and P. Luger. Ibid. 113, 910 (1991).
7. G. Stork and S.D. Rychnovsky. J.Am.Chem.Soc. 109, 1565 (1987). See also: J. Mulzer, H.M. Kirstein, J. Buschmann, C. Lehmann and P. Luger. Ibid. 113, 910 (1991).
8. T. Dorel and P. E. Verkade. Rec. Trav. Chim. Pays-Bos 68, 619 (1949); 70, 35 (1951).
9. T. Dorel and P. E. Verkade. Rec. Trav. Chim. Pays-Bos 68, 619 (1949); 70, 35 (1951).
10. A. Warm and P. Vogel. J.Org.Chem. 51, 5348 (1986). Y. Chen and P. Vogel. J.Org.Chem. 59, 2487 (1994).
11. A. Warm and P. Vogel. J.Org.Chem. 51, 5348 (1986). Y. Chen and P. Vogel. J.Org.Chem. 59, 2487 (1994).
12. O. Arjona, R. Fernández de la Pradilla, A. Mallo, J. Plumet and A. Viso. Tetrahedron Lett. 31, 1475 (1990). O. Arjona, A. Martin-Domenech and J. Plumet. J.Org.Chem. 58, 7929 (1993). See also: M. Lautens. Synlett 177 (1993). M. Lautens, C. Gajda and P. Chiu. J.Chem.Soc.,Chem.Commun. 1193 (1993).
13. O. Arjona, R. Fernández de la Pradilla, A. Mallo, J. Plumet and A. Viso. Tetrahedron Lett. 31, 1475 (1990). O. Arjona, A. Martin-Domenech and J. Plumet. J.Org.Chem. 58, 7929 (1993). See also: M. Lautens. Synlett 177 (1993). M. Lautens, C. Gajda and P. Chiu. J.Chem.Soc.,Chem.Commun. 1193 (1993).
14. O. Arjona, R. Fernández de la Pradilla, A. Mallo, J. Plumet and A. Viso. Tetrahedron Lett. 31, 1475 (1990). O. Arjona, A. Martin-Domenech and J. Plumet. J.Org.Chem. 58, 7929 (1993). See also: M. Lautens. Synlett 177 (1993). M. Lautens, C. Gajda and P. Chiu. J.Chem.Soc.,Chem.Commun. 1193 (1993).
15. O. Arjona, R. Fernández de la Pradilla, A. Mallo, J. Plumet and A. Viso. Tetrahedron Lett. 31, 1475 (1990). O. Arjona, A. Martin-Domenech and J. Plumet. J.Org.Chem. 58, 7929 (1993). See also: M. Lautens. Synlett 177 (1993). M. Lautens, C. Gajda and P. Chiu. J.Chem.Soc.,Chem.Commun. 1193 (1993).
16. M. Bialecki and P. Vogel. Tetrahedron Lett. 35 5213 (1994).
17. W. P. Griffith, S.V. Ley, O.P. Whitcombe and A.D. White. J.Chem.Soc.,Chem.Commun. 1625 (1987).
18. For related systems, see e.g.: W.R. Roush. J.Org.Chem. 56, 4151 (1991).
19. Ph. Kernen and P. Vogel. In preparation.
20. Bicyclic systems had been used before us to generate polypropionates, see e.g.: S. Masamune, H. Yamamoto, S. Kamata and A. Fukuzawa. J.Am.Chem.Soc. 97, 3513 (1975). S. Masamune, C.U. Kim, K.E. Wilson, G.O. Spessard. P.E. Georghiou and G.S. Bates. Ibid. 97, 3512 (1975). P.A. Grieco, J. Inanaga, N.-H. Lin and T. Yanami. J.Am.Chem.Soc. 104, 5781 (1982). J.D. White and Y. Fukuyama. J.Am.Chem.Soc. 101, 226 (1979). M. Lautens, P. Chiu and J.T. Colucci Angew.Chem.Int.Ed.Engl. 32, 281 (1993).
21. Bicyclic systems had been used before us to generate polypropionates, see e.g.: S. Masamune, H. Yamamoto, S. Kamata and A. Fukuzawa. J.Am.Chem.Soc. 97, 3513 (1975). S. Masamune, C.U. Kim, K.E. Wilson, G.O. Spessard. P.E. Georghiou and G.S. Bates. Ibid. 97, 3512 (1975). P.A. Grieco, J. Inanaga, N.-H. Lin and T. Yanami. J.Am.Chem.Soc. 104, 5781 (1982). J.D. White and Y. Fukuyama. J.Am.Chem.Soc. 101, 226 (1979). M. Lautens, P. Chiu and J.T. Colucci Angew.Chem.Int.Ed.Engl. 32, 281 (1993).
22. Bicyclic systems had been used before us to generate polypropionates, see e.g.: S. Masamune, H. Yamamoto, S. Kamata and A. Fukuzawa. J.Am.Chem.Soc. 97, 3513 (1975). S. Masamune, C.U. Kim, K.E. Wilson, G.O. Spessard. P.E. Georghiou and G.S. Bates. Ibid. 97, 3512 (1975). P.A. Grieco, J. Inanaga, N.-H. Lin and T. Yanami. J.Am.Chem.Soc. 104, 5781 (1982). J.D. White and Y. Fukuyama. J.Am.Chem.Soc. 101, 226 (1979). M. Lautens, P. Chiu and J.T. Colucci Angew.Chem.Int.Ed.Engl. 32, 281 (1993).
23. Bicyclic systems had been used before us to generate polypropionates, see e.g.: S. Masamune, H. Yamamoto, S. Kamata and A. Fukuzawa. J.Am.Chem.Soc. 97, 3513 (1975). S. Masamune, C.U. Kim, K.E. Wilson, G.O. Spessard. P.E. Georghiou and G.S. Bates. Ibid. 97, 3512 (1975). P.A. Grieco, J. Inanaga, N.-H. Lin and T. Yanami. J.Am.Chem.Soc. 104, 5781 (1982). J.D. White and Y. Fukuyama. J.Am.Chem.Soc. 101, 226 (1979). M. Lautens, P. Chiu and J.T. Colucci Angew.Chem.Int.Ed.Engl. 32, 281 (1993).
24. Bicyclic systems had been used before us to generate polypropionates, see e.g.: S. Masamune, H. Yamamoto, S. Kamata and A. Fukuzawa. J.Am.Chem.Soc. 97, 3513 (1975). S. Masamune, C.U. Kim, K.E. Wilson, G.O. Spessard. P.E. Georghiou and G.S. Bates. Ibid. 97, 3512 (1975). P.A. Grieco, J. Inanaga, N.-H. Lin and T. Yanami. J.Am.Chem.Soc. 104, 5781 (1982). J.D. White and Y. Fukuyama. J.Am.Chem.Soc. 101, 226 (1979). M. Lautens, P. Chiu and J.T. Colucci Angew.Chem.Int.Ed.Engl. 32, 281 (1993).
25. G. Arvai, D. Fattori and P. Vogel. Tetrahedron 48, 10621 (1992).