Tetrahedron

Determination of the absolute configuration of the chiral biaryl system in the streptonigrin antibiotics by exciton coupled circular dichroic spectroscopy

S Tennant, RW Rickards

Index: Tennant, Shaun; Rickards, Rodney W. Tetrahedron, 1997 , vol. 53, # 44 p. 15101 - 15114

Full Text: HTML

Citation Number: 12

Abstract

The absolute configuration of the chiral phenylpyridyl segment of the Actinomycete antibiotic streptonigrin (1) is defined as R by analysis of the exciton coupled circular dichroic spectra of selected derivatives. The absolute configuration of the co-occurring 10′-O- demethylstreptonigrin (2) is assigned as R by chiroptical correlation with streptonigrin. Circular dichroic spectroscopy indicates that the related phenylpyridone streptonigrone (5) ...

~87%

Total synthesis of streptonigrin

[Basha, Fatima Z.; Hibino, Satoshi; Kim, Deukjoon; Pye, Walter E.; Wu, Tai-Teh; Weinreb, Steven M. Journal of the American Chemical Society, 1980 , vol. 102, # 11 p. 3962 - 3964]

Total synthesis of the antitumor antibiotic streptonigrin

[Weinreb,S.M.; Basha,F.Z.; Hibino,S. Journal of the American Chemical Society, 1982 , vol. 104, p. 536]