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Enantioselective synthesis of a hydroxymethyl-cis-1,3-cyclopentenediol building block.

ABSTRACT: A brief, enantioselective synthesis of a hydroxymethyl-cis-1,3-cyclopentenediol building block is presented. This scaffold allows access to the cis-1,3-cyclopentanediol fragments found in a variety of biologically active natural and non-natural products. This rapid and efficient synthesis is highlighted by the utilization of the palladium-catalyzed enantioselective allylic alkylation of dioxanone substrates to prepare tertiary alcohols.

SUBMITTER: Craig RA 

PROVIDER: S-EPMC3506031 | biostudies-literature | 2012 Nov

REPOSITORIES: biostudies-literature

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Enantioselective synthesis of a hydroxymethyl-cis-1,3-cyclopentenediol building block.

Craig Robert A RA   Roizen Jennifer L JL   Smith Russell C RC   Jones Amanda C AC   Stoltz Brian M BM  

Organic letters 20121026 22

A brief, enantioselective synthesis of a hydroxymethyl-cis-1,3-cyclopentenediol building block is presented. This scaffold allows access to the cis-1,3-cyclopentanediol fragments found in a variety of biologically active natural and non-natural products. This rapid and efficient synthesis is highlighted by the utilization of the palladium-catalyzed enantioselective allylic alkylation of dioxanone substrates to prepare tertiary alcohols. ...[more]

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