Expedient synthesis of N-methyl tubulysin analogues with high cytotoxicity

AW Patterson, HM Peltier…

Index: Peltier, Hillary M.; McMahon, Jeffrey P.; Patterson, Andrew W.; Ellman, Jonathan A. Journal of the American Chemical Society, 2006 , vol. 128, # 50 p. 16018 - 16019

Full Text: HTML

Citation Number: 50

Abstract

An optimized and highly efficient synthesis of potent, bioactive N-methyl tubulysin analogues 2 and 4 has been achieved with> 40% overall yields. This synthesis represents a significant improvement over previously reported syntheses of these and related tubulysin analogues. The stereoselective synthesis of the unnatural amino acid tubuvaline is accomplished using tert-butanesulfinamide chemistry. N-Alkylation to form N-methyl tubuvaline is performed ...