Efficient enantioselective synthesis of a β-hydroxyepoxide building block for the construction of macrocyclic natural products

Tetrahedron Letters

Volumn 39, Issue 10, 1998, Pages 1143-1144

  Schlede, Ulrich ^a   Nazaré, Marc ^a   Waldmann, Herbert ^a  

^a UNIVERSITY OF KARLSRUHE   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOMYCIN; MACROCYCLIC COMPOUND; MACROLIDE;

ARTICLE; ENANTIOMER; OXIDATION; PARTIAL DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0032485225     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10874-7     Document Type: Article

References (19)

1. 1) K. Horáková, V. Betina, Neoplasma 1977, 24, 21; J. Bolard, Biochim. Biophys. Acta 1986, 864, 257.
2. 1) K. Horáková, V. Betina, Neoplasma 1977, 24, 21; J. Bolard, Biochim. Biophys. Acta 1986, 864, 257.
3. 2) S.D. Rychnovsky, Chem. Rev. 1995, 95, 2021; R.D. Norcross, I. Paterson, Chem. Rev. 1995, 95, 2041.
4. 2) S.D. Rychnovsky, Chem. Rev. 1995, 95, 2021; R.D. Norcross, I. Paterson, Chem. Rev. 1995, 95, 2041.
5. 3) a) K.C. Nicolaou, N. Winssinger, J.A. Pastor, S. Ninkovic, F. Sarabia, Y. He, D. Vourloumis, Z. Yang, T. Li, P. Giannakakou, E. Hamel, Nature 1997, 387, 268;
6. b) K.C. Nicolaou, D. Vourloumis, T. Li, J. Pastor, N. Winssinger, Y. He, S. Ninkovic, F. Sarabia, H. Vallberg, F. Roschangar, N.P. King, M.R.V. Finlay, P. Giannakakou, P. Verdier-Pinard, E. Hamel, Angew. Chem. 1997, 109, 2181; Angew. Chem. Int. Ed. Engl. 1997, 36, 2097.
7. b) K.C. Nicolaou, D. Vourloumis, T. Li, J. Pastor, N. Winssinger, Y. He, S. Ninkovic, F. Sarabia, H. Vallberg, F. Roschangar, N.P. King, M.R.V. Finlay, P. Giannakakou, P. Verdier-Pinard, E. Hamel, Angew. Chem. 1997, 109, 2181; Angew. Chem. Int. Ed. Engl. 1997, 36, 2097.
8. 4) a) S. Rakhit, K. Singh, J. Antibiot. 1974, 27, 221;
9. b) P. Delmotte, J. Delmotte-Plaquée, Nature 1953, 777, 344;
10. c) S. Grabley, P. Hammann, K. Hütter, R. Kirsch, H. Kluge, R. Thiericke, M. Mayer, A. Zeeck, J. Antibiot. 1992, 45, 1176.
11. 5) A.W. Ayer, S.P. Lee, A. Tsuneda, Y. Hiratsuka, Can. J. Microbiol. 1980, 26, 766.
12. 6) For alternative syntheses of 8 see: a) E. Hungerbühler, D. Seebach, D. Wasmuth, Helv. Chim. Acta 1981, 64, 1467;
13. b) G.E. Keck, A. Palani, S.F. McHardy, J. Org. Chem. 1994, 59, 3113.
14. 7) M.A Blanchette, W. Choy, J.T. Davis, A.P. Essenfeld, S. Masamune, W.R. Roush, Tetrahedron Lett. 1984, 25, 2183.
15. 8) R.A Johnson, K.B. Sharpless in I. Ojima (ed.), "Catalytic Asymmetric Synthesis", VCH, Weinheim 1993, 227.
16. 3): δ (ppm) = -3.05, -2.53, 18.43, 18.51, 20.04, 20.17, 23.48, 24.65, 34.02, 40.84, 54.12, 58.56, 66.05, 198.31. IR (film): 2960, 2868, 1733, 1466, 1440, 1379, 1252, 1211, 1142, 1128, 1106, 1077, 1032, 997, 969, 875, 835, 816, 777, 726, 679, 662.
17. 10) a) Resolution with biocatalysts: K. Drauz, H. Waldmann in "Enzyme Catalysis in Organic Synthesis", VCH, Weinheim, 1995, 165;
18. b) Reduction with biocatalysts: K. Drauz, H. Waldmann in "Enzyme Catalysis in Organic Synthesis", VCH, Weinheim, 1995, 595;
19. c) Asymmetric reduction: H. Takaya, T. Ohta, R. Noyori in I. Ojima (ed.), "Catalytic Asymmetric Synthesis", VCH, Weinheim 1993, 1.