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Tethered aminohydroxylation: synthesis of the ?-amino acid of microsclerodermins A and B.

ABSTRACT: The utility of the tethered aminohydroxylation (TA) has been demonstrated by synthesis of the complex ?-amino acid residue of microsclerodermins A and B. The TA provided a regio- and stereoselective functionalization of a complex homoallylic alcohol. The route includes late-stage introduction of the aliphatic side chain via a cuprate addition and cross metathesis, a tactic designed to render the synthesis applicable to other microsclerodermins.

SUBMITTER: Pullin RD

PROVIDER: S-EPMC4005371 | biostudies-literature | 2013 Nov

REPOSITORIES: biostudies-literature

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Tethered aminohydroxylation: synthesis of the β-amino acid of microsclerodermins A and B.

Pullin Robert D C RD Rathi Akshat H AH Melikhova Ekaterina Y EY Winter Christian C Thompson Amber L AL Donohoe Timothy J TJ

Organic letters 20131016 21

The utility of the tethered aminohydroxylation (TA) has been demonstrated by synthesis of the complex β-amino acid residue of microsclerodermins A and B. The TA provided a regio- and stereoselective functionalization of a complex homoallylic alcohol. The route includes late-stage introduction of the aliphatic side chain via a cuprate addition and cross metathesis, a tactic designed to render the synthesis applicable to other microsclerodermins. ...[more]

PMID: 24131375

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