Nucleophilic addition to π-allyl molybdenum complexes : a synthesis of the C1-C9 fragment of salinomycin

The asymmetric synthesis of the C1-C9 fragment of salinomycin was achieved in eighteen steps using three key transformations:- (a) Sharpless asymmetric epoxidation to introduce the first chiral centres at C2 and C3; (b) 1,4-Asymmetric induction to create the chiral centre at C6 in a thermodynamicall...

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Bibliographic Details
Main Author Procter, Martin James
Format Dissertation
LanguageEnglish
Published University of Southampton 1996
Subjects
Natural products
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Summary:The asymmetric synthesis of the C1-C9 fragment of salinomycin was achieved in eighteen steps using three key transformations:- (a) Sharpless asymmetric epoxidation to introduce the first chiral centres at C2 and C3; (b) 1,4-Asymmetric induction to create the chiral centre at C6 in a thermodynamically controlled intramolecular cyclisation; (c) Reductive lithiation followed by nucleophilic addition to a chiral π-allyl molybdenum complex to control the configuration at C7 and C8.
Bibliography:0000000135022283