A total synthesis of polyether antibiotic (−)-A23187 (calcimycin)

作者: David P Negri , Yoshito Kishi

DOI: 10.1016/S0040-4039(00)95911-2

关键词: StereospecificityCalcimycinTotal synthesisEnantiomerChemistryBicyclic moleculeAcetalAntibiotic A23187StereochemistryKetone

摘要: Abstract A total synthesis of (−)-A23187 (calcimycin) was accomplished by a convergent approach. The key step the stereospecific cyclization β-hydroxy ketone into spiroketal under basic conditions.

参考文章(18)
Stephen J. Angyal, The composition of reducing sugars in solution Advances in Carbohydrate Chemistry and Biochemistry. ,vol. 42, pp. 15- 68 ,(1984) , 10.1016/S0065-2318(08)60122-5
D. A. Evans, C. E. Sacks, W. A. Kleschick, T. R. Taber, Polyether antibiotics synthesis. Total synthesis and absolute configuration of the ionophore A-23187 Journal of the American Chemical Society. ,vol. 101, pp. 6789- 6791 ,(1979) , 10.1021/JA00516A069
Steven R. Schow, Jonathan D. Bloom, Andrew S. Thompson, Kevin N. Winzenberg, Amos B. Smith, Milbemycin-avermectin studies. 5. Total synthesis of milbemycin .beta.3 and its C(12) epimer Journal of the American Chemical Society. ,vol. 108, pp. 2662- 2674 ,(1986) , 10.1021/JA00270A027
Wolfgang Oppolzer, Martin Petrzilka, An Enantioselective Total Synthesis of Natural (+)‐Luciduline Helvetica Chimica Acta. ,vol. 61, pp. 2755- 2762 ,(1978) , 10.1002/HLCA.19780610802
Teruaki Mukaiyama, Koichi Narasaka, Masayasu Furusato, Convenient synthesis of 1,4-diketones. Application to the synthesis of dihydrojasmone Journal of the American Chemical Society. ,vol. 94, pp. 8641- 8642 ,(1972) , 10.1021/JA00779A091
Herbert O. House, William F. Fischer, Chemistry of carbanions. XVII. Addition of methyl organometallic reagents to cyclohexenone derivatives Journal of Organic Chemistry. ,vol. 33, pp. 949- 956 ,(1968) , 10.1021/JO01267A004
Stephen. Hanessian, Antonio. Ugolini, Daniel. Dube, Paul J. Hodges, Christiane. Andre, Synthesis of (+)-avermectin B1a Journal of the American Chemical Society. ,vol. 108, pp. 2776- 2778 ,(1986) , 10.1021/JA00270A059
Yoshiaki Nakahara, Akira Fujita, Tomoya Ogawa, Total Synthesis of Antibiotic A23187 (Calcimycin) from D-Glucose: Communication Journal of Carbohydrate Chemistry. ,vol. 3, pp. 487- 492 ,(1984) , 10.1080/07328308408057911
SJ Angyal, GS Bethell, Conformational analysis in carbohydrate chemistry. III. The 13C N.M.R. spectra of the hexuloses Australian Journal of Chemistry. ,vol. 29, pp. 1249- 1265 ,(1976) , 10.1071/CH9761249