Difficult Macrocyclizations: New Strategies for Synthesizing Highly Strained Cyclic Tetrapeptides
Author(s)
Meutermans, Wim D. F.
Bourne, Gregory T.
Golding, Simon W.
Horton, Douglas A.
Campitelli, Marc R.
Craik, David
Scanlon, Martin
Smythe, Mark L.
Griffith University Author(s)
Year published
2003
Metadata
Show full item recordAbstract
Cyclic tetrapeptides are an intriguing class of natural products. To synthesize highly strained cyclic tetrapeptides we developed a macrocyclization strategy that involves the inclusion of 2-hydroxy-6-nitrobenzyl (HnB) group at the N-terminus and in the "middle" of the sequence. The N-terminal auxiliary performs a ring closure/ring contraction role, and the backbone auxiliary promotes cis amide bonds to facilitate the otherwise difficult ring contraction. Following this route, the all-L cyclic tetrapeptide cyclo-[Tyr-Arg-Phe-Ala] was successfully prepared.Cyclic tetrapeptides are an intriguing class of natural products. To synthesize highly strained cyclic tetrapeptides we developed a macrocyclization strategy that involves the inclusion of 2-hydroxy-6-nitrobenzyl (HnB) group at the N-terminus and in the "middle" of the sequence. The N-terminal auxiliary performs a ring closure/ring contraction role, and the backbone auxiliary promotes cis amide bonds to facilitate the otherwise difficult ring contraction. Following this route, the all-L cyclic tetrapeptide cyclo-[Tyr-Arg-Phe-Ala] was successfully prepared.
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Journal Title
Organic Letters
Volume
5
Issue
15
Publisher URI
Subject
Chemical Sciences