A highly convergent and efficient total synthesis of the potent antitumor polyketide (-)-callystatin A is described. The synthesis required 19 steps from N-propionyl oxazolidinone 23 and produced the desired product in 3.5% overall yield.
The hydroxyethylene dipeptide isosteres L-682,679, L-684,414, L-685,434, and L-685,458 were synthesized in a few steps by a sequence involving an allyltrichlorostannane coupling with an α-amino aldehyde, followed by hydroboration of the corresponding 1,2-syn and 1,2-anti amino alcohols to give the diols, lactonization under TPAP conditions, lactone opening, and peptide coupling with the desired amine or dipeptide amide. The present synthetic approach represents a practical entry to a large range of other dipeptide isosteres.
Organic chemistryOrganic chemistry Z 0200Allyltrichlorostannane Additions to α-Amino Aldehydes: Application to the Total Synthesis of the Aspartyl Protease Inhibitors L-682,679, L-684,414, L-685,434, and L-685,458 -[about 50 refs.]. -(DIAS*, L. C.; DIAZ, G.; FERREIRA, A. A.; MEIRA, P. R. R.; FERREIRA, E.; Synthesis 2003, 4, 603-622; Inst. Quim., Univ. Estadual Campinas, 13083 Campinas, Sao Paulo, Brazil; Eng.) -Lindner 24-243
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