Concerted synthesis of a spirobicyclic type-VI β-turn mimic of Pro-Pro-Pro-NH2

Ashish P. Vartak; Rodney L. Johnson

doi:10.1021/ol0600335

Concerted synthesis of a spirobicyclic type-VI β-turn mimic of Pro-Pro-Pro-NH₂

Ashish P. Vartak
, Rodney L. Johnson

Medicinal Chemistry

Research output: Contribution to journal › Article › peer-review

16 Scopus citations

Abstract

A highly concerted strategy for the synthesis of symmetrical type-VI β-turn mimics was formulated. A proof of concept is presented in the synthesis of a spirobicyclic peptidomimetic of Pro-Pro-Pro-NH₂, compound 6. The formation of an unusual adduct that was encountered in the process also is reported. This approach is potentially general for type-VI β-turn mimics where the i + 1 and i + 2 residues are identical.

Original language	English (US)
Pages (from-to)	983-986
Number of pages	4
Journal	Organic Letters
Volume	8
Issue number	5
DOIs	https://doi.org/10.1021/ol0600335
State	Published - Mar 2 2006

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abstract = "A highly concerted strategy for the synthesis of symmetrical type-VI β-turn mimics was formulated. A proof of concept is presented in the synthesis of a spirobicyclic peptidomimetic of Pro-Pro-Pro-NH2, compound 6. The formation of an unusual adduct that was encountered in the process also is reported. This approach is potentially general for type-VI β-turn mimics where the i + 1 and i + 2 residues are identical.",

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N2 - A highly concerted strategy for the synthesis of symmetrical type-VI β-turn mimics was formulated. A proof of concept is presented in the synthesis of a spirobicyclic peptidomimetic of Pro-Pro-Pro-NH2, compound 6. The formation of an unusual adduct that was encountered in the process also is reported. This approach is potentially general for type-VI β-turn mimics where the i + 1 and i + 2 residues are identical.

AB - A highly concerted strategy for the synthesis of symmetrical type-VI β-turn mimics was formulated. A proof of concept is presented in the synthesis of a spirobicyclic peptidomimetic of Pro-Pro-Pro-NH2, compound 6. The formation of an unusual adduct that was encountered in the process also is reported. This approach is potentially general for type-VI β-turn mimics where the i + 1 and i + 2 residues are identical.

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Concerted synthesis of a spirobicyclic type-VI β-turn mimic of Pro-Pro-Pro-NH₂

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