Total asymmetric synthesis of Seco-acids of 9,12 anhydroerythronolide aglycons

Tetrahedron Letters

Volumn 39, Issue 23, 1998, Pages 4039-4042

  Ainge, Simon W ^a   Vogel, Pierre ^a  

^a UNIVERSITY OF LAUSANNE   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

3,6 EPOXY 4,5 ISOPROPULIDENEDIOXY 2,4,6 TRIMETHYL 7 [(TERT BUTYL) DIMETHYLSILYLOXY]NON 1 YL PHENYLSULFOXIDE; 7 BENZYLOXY 3,5 ISOPROPYLIDENEOXY 4,6 DIEMTHYLHEPTAN 2 ONE; 9,12 ANHYDROERYTHRONOLIDE AGLYCON; ERYTHROMYCIN; HETEROCYCLIC COMPOUND; POLYKETIDE; UNCLASSIFIED DRUG;

ARTICLE; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0032482528     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00691-1     Document Type: Article

References (26)

1. [1] Chadwick DJ, Goode J, editors. Antibiotic Resistance: Origins, Evolution, Selection and Spread. Ciba Foundation Symposium 207. Chichester: John Wiley 1997.
2. [2] Morishita A, Yaginuma S. J. Antibiotics 1992;45:607-612.
3. [3] Morishita A, Mutoh N, Ishizawa K, Suzuki T, Yokoiyama S, Yaginuma S. J. Antibiotics 1992;45:613-617.
4. [4] Morishita A, Murofushi S, Mutoh N, Ishizawa K, Yaginuma S. J. Antibiotics 1992;45:809-812.
5. [5] Morishita A, Murofushi S, Mutoh, N, Ishizawa K, Yaginuma S. J. Antibiotics 1992;45:1011-1015.
6. [6] Fagihi R, Freiburg L, Leonard J, Plattner JJ, Lartey PA. J. Antibiotics 1996;49:493-495.
7. [7] See e.g.: Lartey PA, Nellans HN, Faghih R, Petersen A, Edwards CM, Freiburg L, Quigley S, Marsh K, Klein LL, Plattner JJ. J. Med. Chem. 1995;38:1793-1798.
8. [8] See e.g.: Martin SF, Hida T, Kym PR, Loft M, Hodgson A. J. Am. Chem. Soc. 1997;119:3193-3194 and references cited therein. See also: Hanessian S, Wang W, Gai Y, Olivier EJ. J. Am. Chem. Soc. 1997;119:10034-10041. Evans DA, Kim AS. Tetrahedron Lett. 1997;38:53-56.
9. [8] See e.g.: Martin SF, Hida T, Kym PR, Loft M, Hodgson A. J. Am. Chem. Soc. 1997;119:3193-3194 and references cited therein. See also: Hanessian S, Wang W, Gai Y, Olivier EJ. J. Am. Chem. Soc. 1997;119:10034-10041. Evans DA, Kim AS. Tetrahedron Lett. 1997;38:53-56.
10. [8] See e.g.: Martin SF, Hida T, Kym PR, Loft M, Hodgson A. J. Am. Chem. Soc. 1997;119:3193-3194 and references cited therein. See also: Hanessian S, Wang W, Gai Y, Olivier EJ. J. Am. Chem. Soc. 1997;119:10034-10041. Evans DA, Kim AS. Tetrahedron Lett. 1997;38:53-56.
11. [9] Vogel P, Sevin A-F, Kernen P, Bialecki M. Pure Appl. Chem. 1996;68:719-722.
12. [10] a) Sevin A-F, Vogel P. J. Org. Chem. 1994;59:5920-5926;
13. b) Kernen P, Vogel P, Helv. Chim. Acta 1995;78:301-324.
14. [11] Fleming I, Paterson I. Synthesis 1979:736-738.
15. [12] Denmark SE, Edwards, JP. J. Org. Chem. 1991;56:6974-6981.
16. [13] Ito Y, Fujii S, Saegusa T. J. Org. Chem. 1976;41:2073-2074.
17. [14] Clark RD, Heathcock CH. J. Org. Chem. 1976;41:1396-1403.
18. [15] Larock RC, Hightower TR, Kraus GA, Hahn P, Zheng D. Tetrahedron Lett 1995;36:2423-2426.
19. [16] Keinan E, Greenspoon N. J. Am. Chem. Soc. 1986;108:7314-7325.
20. [17] Commins DL, Dehghani A. Tetrahedron Lett. 1992;33:6299-6302.
21. [18] Echavarren AM, Stille JK. J. Am. Chem. Soc. 1987;109:5478-5486.
22. [19] Corey EJ, Hortmann AG. J. Am. Chem. Soc. 1965;87:5736-5742.
23. [20] Mulzer J, Kirstein HM, Buschmann J, Lehmann C, Luger P. J. Am. Chem. Soc. 1991;113:910-923.
24. [21] Paterson I, Norcross RD, Ward RA, Romea P, Lister MA. J. Am. Chem. Soc. 1994;116:11287-11314.
25. [22] Stork G, Paterson I, Lee FKC. J. Am. Chem. Soc. 1982;104:4686.
26. [23] Sviridov AF, Ermolenko MS, Yashunsky DV, Borodkin VS, Kochetkov NK. Tetrahedron Lett. 1987;28:3835-3838.