Enantiocontrolled Synthesis of Spirooxindoles Based on the [5 + 2] Cycloaddition of a Tp(CO)2Mo(pyridinyl) Scaffold (Tp = Hydridotrispyrazolylborate)

作者: Helena C. Malinakova , Lanny S. Liebeskind

DOI: 10.1021/OL000313Z

关键词:

摘要: A [5 + 2] cycloaddition of the pyridinyl π-complex (−)-1 (98% ee) to methyleneoxindole 2 afforded spirooxindole complex (−)-3 in high enantiomeric purity. Complex was converted pyrrolidine (−)-8 (97% ee), which is related potent cytotoxic analogues spirotryprostatins alkaloids.

参考文章(22)
A. Krief, D. Surleraux, H. Frauenrath, Novel stereoselective route to cis-chrysanthemic acid Tetrahedron Letters. ,vol. 29, pp. 6157- 6160 ,(1988) , 10.1016/S0040-4039(00)82293-5
R. L. Hinman, C. P. Bauman, Reactions of 3-Bromooxindoles. The Synthesis of 3-Methyleneoxindole1 The Journal of Organic Chemistry. ,vol. 29, pp. 2431- 2437 ,(1964) , 10.1021/JO01031A080
James M. Cook, Sean P. Hollinshead, Desir仔 S. Grubisha, Dennis W. Bennett, Studies in the formation of oxindoles from their indoloazabicyclo[3.3.1]nonane counterparts and implications for the biogenesis of alstonisine Heterocycles. ,vol. 29, pp. 529- 537 ,(1989) , 10.3987/COM-89-4839
Robin D. Clark, Clayton H. Heathcock, Synthesis of a cytotoxic vernolepin prototype. Ozonization of silyloxyalkenes. Journal of Organic Chemistry. ,vol. 41, pp. 1396- 1403 ,(1976) , 10.1021/JO00870A023
Haishan Wang, A. Ganesan, A biomimetic total synthesis of (-)-spirotryprostatin B and related studies. Journal of Organic Chemistry. ,vol. 65, pp. 4685- 4693 ,(2000) , 10.1021/JO000306O
Scott D. Edmondson, Samuel J. Danishefsky, The Total Synthesis of Spirotryprostatin A Angewandte Chemie International Edition. ,vol. 37, pp. 1138- 1140 ,(1998) , 10.1002/(SICI)1521-3773(19980504)37:8<1138::AID-ANIE1138>3.0.CO;2-N