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The Total Synthesis of Tubulysin D

2006; American Chemical Society; Volume: 128; Issue: 50 Linguagem: Inglês

10.1021/ja067177z

1943-2984

Hillary M. Peltier, Jeffrey McMahon, Andrew W. Patterson, Jonathan A. Ellman,

Synthetic Organic Chemistry Methods

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.