Hydroxyethylene dipeptide isosteres L-685,434, L-682,679 and L-685,458 were synthesized in a few steps by a sequence involving an allyltrichlorostannane coupling with an a-aminoaldehyde followed by hydroboration of the corresponding 1,2syn and 1,2-anti aminoalcohols to give the diols, lactonization under TPAP conditions, lactone opening and peptide coupling with the desired amine or dipeptide amide.
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
A porção carbocíclica (C11-C21) da Estavamicina foi preparada através de uma sequência envolvendo 11 etapas (10% de rendimento global) a partir do (R)-(-)-3-hidróxi-2-metilpropionato de metila. As etapas chave envolvem um acoplamento de Stille entre uma vinilestanana e um iodeto vinílico, catalisado por complexo de paládio seguido de uma cicloadição de Diels-Alder intramolecular conduzindo ao isômero desejado como produto majoritário juntamente com outros 3 isômeros em 78% de rendimento.The carbocyclic (C11-C21) fragment of Stawamycin has been prepared by a sequence involving 11 steps (10% overall yield) from methyl (R)-(-)-3-hydroxy-2-methylpropionate. Key steps are Pd-catalyzed Stille coupling reaction between a vinyl iodide and a vinylstannane followed by an intramolecular Diels-Alder cycloaddition reaction to afford the desired adduct as the major isomer together with three other possible adducts in 78% overall yield.
Chiral and achiral allyltrichlorostannanes reacted with chiral aldehydes to give the corresponding homoallylic alcohols with good to high diastereoselectivities. This approach has been applied to the synthesis of hydroxyethylene dipeptide isosteres L-682, 679, L-684,414, L-685,434 and L-685,458.
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