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Beyond the Roche ester: a new approach to polypropionate stereotriad synthesis.

ABSTRACT: An efficient, step-economical, and scalable approach to the synthesis of polypropionate stereotriads has been developed. Either 2-butyne or propyne is subjected to rhodium-catalyzed silylformylation and in situ crotylation of the resulting aldehydes. Tamao oxidation under either "standard" conditions or "aprotic" conditions then delivers the completed stereotriads in a three-step, two-pot sequence. In contrast to the classical Roche ester approach, the ?-stereocenter is obtained for "free."

SUBMITTER: Foley CN

PROVIDER: S-EPMC3993613 | biostudies-literature | 2014 Feb

REPOSITORIES: biostudies-literature

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Beyond the Roche ester: a new approach to polypropionate stereotriad synthesis.

Foley Corinne N CN Leighton James L JL

Organic letters 20140206 4

An efficient, step-economical, and scalable approach to the synthesis of polypropionate stereotriads has been developed. Either 2-butyne or propyne is subjected to rhodium-catalyzed silylformylation and in situ crotylation of the resulting aldehydes. Tamao oxidation under either "standard" conditions or "aprotic" conditions then delivers the completed stereotriads in a three-step, two-pot sequence. In contrast to the classical Roche ester approach, the α-stereocenter is obtained for "free." ...[more]

PMID: 24502345

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