ChemInform Abstract: Total Synthesis of Dehydrodidemnin B. Use of Uronium and Phosphonium Salt Coupling Reagents in Peptide Synthesis in Solution.
Abstract
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ChemInform Abstract
The antiproliferative title compound (Ib) is obtained from didemnin A ( Ia), which was synthesized by 2 routes in 4% and 27% overall yield. The first method is based on the elaboration of a linear heptadepsipeptide incorporating the first amino acid of the didemnin side chain, (R)-N(Me)-Leu. Deprotection of the amino and carboxyl terminii of this linear precursor followed by macrocyclization yields a protected derivative of (Ia). The second route involves the synthesis of the Boc-protected didemnin macrocycle from a linear hexadepsipeptide lacking (R)-N(Me)-Leu. Removal of the Boc group from the macrocycle followed by coupling with Boc-(R)-N(Me)-Leu-OH yields Boc-didemnin A. Extensive use is made of the title coupling agents.
