Total synthesis of (−)-Cryptofolione

Enantioselective total synthesis of δ-lactone containing natural product (−)-cryptofolione was accomplished from commercially available benzylidene acetone. Key features of the synthesis include lipase mediated resolution of a β-hydroxy ketone intermediate, DBU mediated isomerization of γ,δ-unsatura...

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Bibliographic Details
Published in:Tetrahedron 2021-01, Vol.79, p.131842, Article 131842
Main Authors: Vaithegi, Kannan, Prasad, Kavirayani R.
Format: Article
Language:English
Subjects:
Chemoenzymatic synthesis
lactones
Total synthesis
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Summary:Enantioselective total synthesis of δ-lactone containing natural product (−)-cryptofolione was accomplished from commercially available benzylidene acetone. Key features of the synthesis include lipase mediated resolution of a β-hydroxy ketone intermediate, DBU mediated isomerization of γ,δ-unsaturated aldehyde to α,β-unsaturated aldehyde, Brown allylation and RCM reactions. [Display omitted] •Accomplished the total synthesis of (−)-cryptofolione from commercially available benzylidene acetone.•PS AminoLipase mediated resolution of β-hydroxy ketone possessing an allylic alcohol and unsaturated ketone.•Brown’s allylation and RCM were used to construct the lactone component.
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2020.131842