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Synthesis of the dysiherbaine tetrahydropyran core employing a tethered aminohydroxylation reaction.

ABSTRACT: A stereocontrolled and scalable synthesis of an advanced intermediate of the dysiherbaine tetrahydropyran core has been achieved in 11 steps and 27% overall yield. The key feature of this synthetic approach is the application of the Donohoe tethered aminohydroxylation reaction to install the amino diol and establish the four contiguous syn stereocenters on the tetrahydropyran ring.

SUBMITTER: Cohen JL

PROVIDER: S-EPMC1865120 | biostudies-literature | 2007 Apr

REPOSITORIES: biostudies-literature

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Synthesis of the dysiherbaine tetrahydropyran core employing a tethered aminohydroxylation reaction.

Cohen Jamie L JL Chamberlin A Richard AR

Tetrahedron letters 20070401 14

A stereocontrolled and scalable synthesis of an advanced intermediate of the dysiherbaine tetrahydropyran core has been achieved in 11 steps and 27% overall yield. The key feature of this synthetic approach is the application of the Donohoe tethered aminohydroxylation reaction to install the amino diol and establish the four contiguous syn stereocenters on the tetrahydropyran ring. ...[more]

PMID: 17479167

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