Ansa macrolides as molecular workbenches: Stereocontrolled syn additions to E olefins

Angewandte Chemie - International Edition

Volumn 37, Issue 11, 1998, Pages 1566-1569

  Mulzer, Johann ^a   Schein, Karin ^b   Bats, Jan W ^b   Buschmann, Jürgen ^b   Luger, Peter ^b  

^a Institute of Organic Chemistry   (Austria)

^b NONE

Author keywords

Diastereoselective reactions; Dihydroxylations; Epoxidations; Macrocycles; Protecting groups

Indexed keywords

EID: 0032546916     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19980619)37:11<1566::AID-ANIE1566>3.0.CO;2-U     Document Type: Article

References (15)

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6. -1]: (E)-cyclooctene 149, (E)-cyclononene 84, (E)-cyclodecene 45; A. C. Cope, B. A. Pawson, J. Am. Chem. Soc. 1965, 87, 3649-3651; A. C. Cope, K. Banholzer, H. Keller, B. A. Pawson, J. J. Whang, H. J. S. Winkler, ibid. 1965, 87, 3644-3649; G. Binsch, J. D. Roberts, ibid. 1965, 87, 5157-5162.
7. -1]: (E)-cyclooctene 149, (E)-cyclononene 84, (E)-cyclodecene 45; A. C. Cope, B. A. Pawson, J. Am. Chem. Soc. 1965, 87, 3649-3651; A. C. Cope, K. Banholzer, H. Keller, B. A. Pawson, J. J. Whang, H. J. S. Winkler, ibid. 1965, 87, 3644-3649; G. Binsch, J. D. Roberts, ibid. 1965, 87, 5157-5162.
8. -1]: (E)-cyclooctene 149, (E)-cyclononene 84, (E)-cyclodecene 45; A. C. Cope, B. A. Pawson, J. Am. Chem. Soc. 1965, 87, 3649-3651; A. C. Cope, K. Banholzer, H. Keller, B. A. Pawson, J. J. Whang, H. J. S. Winkler, ibid. 1965, 87, 3644-3649; G. Binsch, J. D. Roberts, ibid. 1965, 87, 5157-5162.
9. Additions to ansa alkenes: P. K. Chowdhury, A. Prelle, D. Schomburg, M. Thielmann, E. Winterfeldt, Liebigs Ann. Chem. 1987, 1095-1099; summary: E. Winterfeldt, Chimia 1993, 47, 39-45; diastereoselective addition to double bonds in macrocycles: W. C. Still, L. J. MacPherson, T. Harada, J. F. Callahan, A. L. Rheingold, Tetrahedron 1984, 40, 2275-2281.
10. Additions to ansa alkenes: P. K. Chowdhury, A. Prelle, D. Schomburg, M. Thielmann, E. Winterfeldt, Liebigs Ann. Chem. 1987, 1095-1099; summary: E. Winterfeldt, Chimia 1993, 47, 39-45; diastereoselective addition to double bonds in macrocycles: W. C. Still, L. J. MacPherson, T. Harada, J. F. Callahan, A. L. Rheingold, Tetrahedron 1984, 40, 2275-2281.
11. Additions to ansa alkenes: P. K. Chowdhury, A. Prelle, D. Schomburg, M. Thielmann, E. Winterfeldt, Liebigs Ann. Chem. 1987, 1095-1099; summary: E. Winterfeldt, Chimia 1993, 47, 39-45; diastereoselective addition to double bonds in macrocycles: W. C. Still, L. J. MacPherson, T. Harada, J. F. Callahan, A. L. Rheingold, Tetrahedron 1984, 40, 2275-2281.
12. J. Inanaga, K. Hirata, H. Saeki, T. Katsuki, Y. Yamaguchi, Bull. Chem. Soc. Jpn. 1979, 52, 1989-1993.
13. Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-100826. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB21EZ, UK (fax: int. code + (44) 1223-336033; e-mail: deposit@ccdc.cam.ac.uk).
14. M. Schelhaas, H. Waldmann, Angew. Chem. 1996, 108, 2192-2219; Angew. Chem. Int. Ed. Engl. 1996, 35, 2056-2083.
15. M. Schelhaas, H. Waldmann, Angew. Chem. 1996, 108, 2192-2219; Angew. Chem. Int. Ed. Engl. 1996, 35, 2056-2083.