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Hydroxyl-substituted ladder polyethers via selective tandem epoxidation/cyclization sequence.

ABSTRACT: A new and highly selective method for the synthesis of hydroxyl-substituted tetrahydropyrans is described. This method utilizes titanium(IV) isopropoxide and diethyl tartrate to perform a diastereoselective epoxidation followed by in situ epoxide activation and highly selective endo-cyclization to form the desired tetrahydropyran ring. The HIJ ring fragment of the marine ladder polyether yessotoxin was synthesized using this two-stage tactic that proceeds with high efficiency and excellent regioselectivity.

SUBMITTER: Czabaniuk LC

PROVIDER: S-EPMC4444367 | biostudies-literature | 2015 Feb

REPOSITORIES: biostudies-literature

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Hydroxyl-substituted ladder polyethers via selective tandem epoxidation/cyclization sequence.

Czabaniuk Lara C LC Jamison Timothy F TF

Organic letters 20150203 4

A new and highly selective method for the synthesis of hydroxyl-substituted tetrahydropyrans is described. This method utilizes titanium(IV) isopropoxide and diethyl tartrate to perform a diastereoselective epoxidation followed by in situ epoxide activation and highly selective endo-cyclization to form the desired tetrahydropyran ring. The HIJ ring fragment of the marine ladder polyether yessotoxin was synthesized using this two-stage tactic that proceeds with high efficiency and excellent regio ...[more]

PMID: 25647091

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