Tetrahedron

Synthese de la Dolastatine 10 et de la [R-Doe]-Dolastatine 10

F Roux, I Maugras, J Poncet, G Niel, P Jouin

Index: Roux, Florence; Maugras, Isabelle; Poncet, Joel; Niel, Gilles; Jouin, Patrick Tetrahedron, 1994 , vol. 50, # 18 p. 5345 - 5360

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Citation Number: 46

Abstract

A stepwise synthesis of dolastatin 10 starting from the dolaphenine residue is described. The chiral dola isoleuine and dolaproine residues were obtained by 5-step procedures from the corresponding N-Boc amino acid. The key steps are respectively the NaBH4 reduction of an allylic ketone and the addition of an achiral Z-crotylboronate on the N-Boc-L-prolinal. Peptidic couplings were efficiently realised with reagents developed in the laboratory.