Stereoselective Synthesis of Optically Active 4-Ethyl-3,5-dihydroxy-2-methylpentyl Derivatives. A Basic Building Block with Three Contiguous Chiral Centers of Poly ether Antibiotics

Chemical and Pharmaceutical Bulletin

Volumn 41, Issue 11, 1993, Pages 2044-2046

  Horita, Kiyoshi ^a   Tanaka, Kazuhiro ^a   Yonemitsu, Osamu ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

asymmetric epoxidation; chiral synthon; organocopper reagent; polyether antibiotic; protecting group; stereoselective synthesis

Indexed keywords

ISOLASALOCID A; LASALOCID; LYSOCELLIN; POLYETHER ANTIBIOTIC AGENT; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0027745847     PISSN: 00092363     EISSN: 13475223     Source Type: Journal    
DOI: 10.1248/cpb.41.2044     Document Type: Article

References (13)

1. K. Horita, I. Noda, K. Tanaka, Y. Oikawa, O. Yonemitsu, Tetrahedron, 49, 5997 (1993).
2. M.R. Johnson, T. Nakata, Y. Kishi, Tetrahedron Lett., 1979, 4343.
3. H. Nagaoka, Y. Kishi, Tetrahedron, 37, 3873 (1981).
4. Y. Oikawa, T. Nishi, H. Itaya, O. Yonemitsu, Tetrahedron Lett., 24, 1987 (1983).
5. T. Nakata, M. Fukui, H. Ohtsuka, T. Oishi, Tetrahedron Lett., 24, 2661 (1983).
6. K. Suzuki, E. Katayama, K. Tomooka, T. Matsumoto, G. Tsuchihashi, Tetrahedron Lett., 26, 3707 (1985).
7. K. Horita, Y. Oikawa, O. Yonemitsu, Chem. Pharm. Bull., 37, 1698 (1989).
8. I. Noda, K. Horita, Y. Oikawa, O. Yonemitsu, Tetrahedron Lett., 31, 6035 (1990).
9. A.G.M. Barrett, J.J. Edmunds, K. Horita, C.J. Parkinson, J. Chem. Soc., Chem. Commun., 1992, 1236.
10. Y. Gao, R.M. Hanson, J.M. Klunder, S.Y. Ko, H. Masamune, K.B. Sharpless, J. Am. Chem. Soc., 109, 5765 (1987).
11. C. Huynh, F.D. Boumechal, G. Linstrumelle, Tetrahedron Lett., 20, 1503 (1979).
12. E.J. Corey, F.J. Hannon, N.W. Boaz, Tetrahedron, 45, 545 (1989).
13. K. Horita, K. Tanaka, T. Inoue, O. Yonemitsu, Tetrahedron Lett., 33, 5441 (1992).