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Stereoselective synthesis of the C9-C19 fragment of lyngbyaloside B and C via ether transfer.

ABSTRACT: A stereoselective synthesis of the C9-C19 fragment of lyngbyaloside B and C highlighted, by an extension of our ether transfer methodology, enables the formation of tertiary ethers. 2-Naphthylmethyl ethers have been shown to proceed efficiently through ether transfer with high stereoselectivity and are easily deprotected by DDQ oxidation. Variation of the workup conditions results in the stereoselective formation of syn-1,3-diol mono- or diethers.

SUBMITTER: Stefan E

PROVIDER: S-EPMC3391344 | biostudies-literature | 2012 Jul

REPOSITORIES: biostudies-literature

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Stereoselective synthesis of the C9-C19 fragment of lyngbyaloside B and C via ether transfer.

Stefan Eric E Taylor Richard E RE

Organic letters 20120620 13

A stereoselective synthesis of the C9-C19 fragment of lyngbyaloside B and C highlighted, by an extension of our ether transfer methodology, enables the formation of tertiary ethers. 2-Naphthylmethyl ethers have been shown to proceed efficiently through ether transfer with high stereoselectivity and are easily deprotected by DDQ oxidation. Variation of the workup conditions results in the stereoselective formation of syn-1,3-diol mono- or diethers. ...[more]

PMID: 22716968

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