A highly efficient, asymmetric synthesis of blastidic acid: the β-amino acid component of the antibiotic,(+)-blasticidin S
R Bischoff, N McDonald, A Sutherland
Index: Bischoff, Roland; McDonald, Niall; Sutherland, Andrew Tetrahedron Letters, 2005 , vol. 46, # 42 p. 7147 - 7149
Full Text: HTML
Citation Number: 13
Abstract
A new approach for the asymmetric synthesis of blastidic acid, the β-amino acid component of the antibiotic,(+)-blasticidin S has been achieved in 11 steps and 30% overall yield. The key transformations involve a one-pot Swern/Wittig reaction sequence to prepare the carbon backbone followed by a stereoselective conjugate addition to introduce the β-amino functionality.
Related Articles:
Supramolecular gelation of alcohol and water by synthetic amphiphilic gallic acid derivatives
[Tamiaki, Hitoshi; Ogawa, Keishiro; Enomoto, Keisuke; Taki, Kazutaka; Hotta, Atsushi; Toma, Kazunori Tetrahedron, 2010 , vol. 66, # 9 p. 1661 - 1666]
Synthesis of β-amino arylketones through the addition of ArLi derivatives to β-aminoesters
[Lima, Paulo G.; Sequeira, Lucia C.; Costa, Paulo R.R. Tetrahedron Letters, 2001 , vol. 42, # 21 p. 3525 - 3527]
Synthesis and biological evaluation of analogues of the marine cyclic depsipeptide obyanamide
[Zhang, Wei; Ding, Ning; Li, Yingxia Journal of Peptide Science, 2011 , vol. 17, # 7 p. 533 - 539]
[Soares, Ana M. S.; Costa, Susana P. G.; Goncalves, M. Sameiro T. Amino Acids, 2010 , vol. 39, # 1 p. 121 - 133]