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2005
Peptides
U 0400
02- 197
Stereoselective Mn-Mediated Coupling of Functionalized Iodides and Hydrazones: A Synthetic Entry to the Tubulysin α-Amino Acids. — A novel C—C bond
construction approach to the synthesis of α,γ-disubstituted α-amino acids is developed.
It provides access to enantiomerically pure building blocks for the total synthesis of
tubulysins. Key step is a highly stereoselective Mn-mediated coupling of an alkyl
iodide and a hydrazone. The building blocks (VII) and (VIII) for tubulysin D are prepared in 4 steps from (III) and (VI), respectively. — (FRIESTAD*, G. K.; MARIE,
J.-C.; DEVEAU, A. M.; Org. Lett. 6 (2004) 19, 3249-3252; Dep. Chem., Univ. Vt.,
Burlington, VT 05405, USA; Eng.) — Steudel
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