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Synthesis of a tetrasubstituted tetrahydronaphthalene scaffold for ?-helix mimicry via a MgBr2-catalyzed Friedel-Crafts epoxide cycloalkylation.

ABSTRACT: ?-Helices are ubiquitous protein recognition elements that bind diverse biomolecular targets. The synthesis of a small molecule scaffold to present the side chains of an ?-helix is described. The 1,3,5,7-tetrasubstituted 1,2,3,4-tetrahydronaphthalene scaffold, providing mimicry of the i, i+3, and i+4 positions of an ?-helix, was synthesized using a novel MgBr2-catalyzed Friedel-Crafts epoxide cycloalkylation as the key step. Each position may be differentiated via O-alkylation after scaffold synthesis, generating a diversity-oriented approach to readily synthesize proteomimetics for different targets.

SUBMITTER: Naduthambi D

PROVIDER: S-EPMC4209909 | biostudies-literature | 2013 Sep

REPOSITORIES: biostudies-literature

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Synthesis of a tetrasubstituted tetrahydronaphthalene scaffold for α-helix mimicry via a MgBr2-catalyzed Friedel-Crafts epoxide cycloalkylation.

Naduthambi Devan D Bhor Santosh S Elbaum Michael B MB Zondlo Neal J NJ

Organic letters 20130909 18

α-Helices are ubiquitous protein recognition elements that bind diverse biomolecular targets. The synthesis of a small molecule scaffold to present the side chains of an α-helix is described. The 1,3,5,7-tetrasubstituted 1,2,3,4-tetrahydronaphthalene scaffold, providing mimicry of the i, i+3, and i+4 positions of an α-helix, was synthesized using a novel MgBr2-catalyzed Friedel-Crafts epoxide cycloalkylation as the key step. Each position may be differentiated via O-alkylation after scaffold syn ...[more]

PMID: 24016333

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