The total synthesis of tubulysin D.
The first total synthesis of tubulysin D is reported. The development and application of new tert-butanesulfinamide methods allowed for rapid syntheses of the tubuvaline and tubuphenylalanine fragments. Most significantly, a route was devised and implemented to introduce and carry forward the highly labile N,O-acetal functionality. Tubulysin D is the most active member of the tubulysin family, and the efficient synthetic route described herein will allow for the rapid syntheses of analogues to probe the biological activity of this important class of natural products.
Peltier
Hillary M
HM
Department of Chemistry, University of California, Berkeley, California 94720, USA.
McMahon
Jeffrey P
JP
Patterson
Andrew W
AW
Ellman
Jonathan A
JA
D015394:Molecular Structure; D009842:Oligopeptides / Q000138:chemical synthesis* / Q000737:chemistry
D009842:Oligopeptides; C502386:tubulysin D