N,O-isopropylidenated threonines as tools for peptide cyclization

Application to the synthesis of mahafacyclin B

Nima Sayyadi, Danielle Skropeta, Katrina A. Jolliffe*

*Corresponding author for this work

Research output: Contribution to journalArticle

29 Citations (Scopus)

Abstract

(Chemical Equation Presented) The influence of a single N,O-isopropylidenated threonine turn-inducer on the cyclization of a linear heptapeptide precursor to mahafacyclin B has been investigated. Incorporation of an N,O-isopropylidenated threonine more than doubles the head-to-tail cyclization yield. The N,O-isopropylidene grouping is then readily disassembled to give the antimalarial cyclic peptide in high yield.

Original languageEnglish
Pages (from-to)5497-5499
Number of pages3
JournalOrganic Letters
Volume7
Issue number24
DOIs
Publication statusPublished - 24 Nov 2005
Externally publishedYes

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