Asymmetric synthesis of non‐proteinogenic dipeptides by the bislactim ether method, I. Asymmetric synthesis of Boc‐L‐Val‐(R)‐α‐MePro‐OMe, Boc‐L‐Val‐(R)‐Pro‐OMe, and of Boc‐L‐Val‐(R)‐α‐MePhe‐OMe, Ac‐L‐Val‐(R)‐α‐MePhe‐OMe and their analogues. A new strategy for the synthesis of non‐proteinogenic dipeptides

Abstract

AbstractA new strategy for the asymmetric synthesis of non‐proteinogenic dipeptides based on the bislactim ether method is described. The non‐proteinogenic amino acid which is part of the dipeptide, is built up stereoselectively at the bislactim ether stage. Subsequently, the bislactim ether is partially cleaved to a monolactim ether. This, in turn, is converted into a dipeptide ester with the non‐proteinogenic amino acid either in C‐ or in N‐terminal position. The title compounds were synthesized by this new strategy.