Journal of Organic Chemistry 2009-06-05

Straightforward stereoselective access to cyclic peptidomimetics.

Santos Fustero, Natalia Mateu, Laia Albert, José Luis Aceña

Index: J. Org. Chem. 74(11) , 4429-32, (2009)

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Abstract

The preparation of cyclic dipeptide mimetics from chiral imino lactones derived from (R)-phenylglycinol is described. Key steps of the synthetic route included the fully stereoselective construction of a quaternary center, the formation of six-, seven-, or eight-membered lactams by means of an RCM cyclization, and the introduction of a new amino group within the lactam ring. The synthesis of a tripeptide mimetic is also reported.