Artículos de revistas
Total Synthesis Of 10-deoxymethynolide, The Aglycon Of The Macrolide Antibiotic 10-deoxymethymycin
Registro en:
Journal Of Organic Chemistry. , v. 63, n. 22, p. 7811 - 7819, 1998.
223263
10.1021/jo9809433
2-s2.0-0032582735
Autor
Pilli R.A.
De Andrade C.K.Z.
Souto C.R.O.
De Meijere A.
Institución
Resumen
A short efficient total synthesis of 10-deoxymethynolide (2c), the aglycon of 10-deoxymethymycin (1c), has been accomplished in 16 steps and 12% overall yield from (S)-3-O-p-toluenesulfonyl-3-hydroxy-2-methylpropanal (15c). The synthesis features an expeditious preparation of (+)-5a, a synthetic equivalent of the Prelog-Djerassi lactonic acid, and the construction of a 12-membered lactone through an intramolecular Nozaki- Hiyama-Kishi coupling reaction. 63 22 7811 7819 Masamune, S., Bates, G.S., Corcoran, J.W., (1977) Angew. Chem., Int. Ed. Engl., 16, p. 585 Omura, S., (1984) Macrolide Antibiotics: Chemistry, Biology, and Practice Academic Press: Orlando, Fl Paterson, I., Mansuri, M.M., (1985) Tetrahedron, 41, p. 3569 Boeckman, R.H., Goldstein, M., (1988) The Total Synthesis of Natural Products ApSimon, J., Ed. John Wiley & Sons: New York, 7, p. 1 Meng, Q., Hesse, M., (1991) Top. Curr. Chem., 161, p. 107 Lartley, P.A., Nellans, H.N., Tanaka, S.K., (1994) Adv. 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