Tetrahedron p. 5345 - 5360 (1994)
Update date:2022-07-29
Topics:
Roux, Florence
Maugras, Isabelle
Poncet, Joel
Niel, Gilles
Jouin, Patrick
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.
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Doi:10.1016/0040-4039(94)88291-6
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