The stereospecific cyclolization of N-(α-hydroxyacyl)-phenylalanyl-proline lactams

作者: H. Ott , A.J. Frey , A. Hofmann

DOI: 10.1016/S0040-4020(01)99240-3

关键词:

摘要: Abstract The spontaneous ring closure of N-(α-hydroxyacyl)-phenylalanyl proline-lactams to cyclols was shown take a stereospecific course. These facts have made an important contribution the synthesis ergotamine.

参考文章(7)
P.A. Levene, A NEW SYNTHESIS OF 1-AMINO-2-HYDROXYPROPANE Journal of Biological Chemistry. ,vol. 113, pp. 153- 156 ,(1936) , 10.1016/S0021-9258(18)74900-4
Max Bergmann, Josephine E. Tietzman, TRANSFORMATIONS OF AN ACYL DIKETOPIPERAZINE Journal of Biological Chemistry. ,vol. 155, pp. 535- 546 ,(1944) , 10.1016/S0021-9258(18)51184-4
P.A. Levene, Mimosa H. Pfaltz, STUDIES ON RACEMIZATION ACTION OF ALKALI ON DEXTRO-ALANYL-DEXTRO-ALANINE ANHYDRIDE Journal of Biological Chemistry. ,vol. 63, pp. 661- 668 ,(1925) , 10.1016/S0021-9258(18)84979-1
M. Bergmann, L. Zervas, H. Köster, Autoracemisation arginin-haltiger Aminosäure-anhydride. (Beitrag zur Struktur des Clupeins) Berichte der deutschen chemischen Gesellschaft (A and B Series). ,vol. 62, pp. 1901- 1905 ,(1929) , 10.1002/CBER.19290620803
R.G. Griot, A.J. Frey, The formation of cyclols from N-hydroxyacyllactams Tetrahedron. ,vol. 19, pp. 1661- 1673 ,(1963) , 10.1016/S0040-4020(01)99239-7
A. Hofmann, A. J. Frey, H. Ott, The total synthesis of ergotamine Cellular and Molecular Life Sciences. ,vol. 17, pp. 206- 207 ,(1961) , 10.1007/BF02160615
M. Bovarnick, H. T. Clarke, Racemization of Tripeptides and Hydantoins1 Journal of the American Chemical Society. ,vol. 60, pp. 2426- 2430 ,(1938) , 10.1021/JA01277A036