Total Synthesis of (±) Pimeforazine A and B

Shireen Aaisha Saeed; Faiz Ahmed Khan

doi:10.1055/a-2698-0726

Synlett, Table of Contents

Synlett
DOI: 10.1055/a-2698-0726

Letter

Published as part of the Special Issue dedicated to Prof. S. Chandrasekaran on his 80th birthday

Total Synthesis of (±) Pimeforazine A and B

Authors

Shireen Aaisha Saeed

¹Department of Chemistry, Indian Institute of Technology Hyderabad, Kandi, Sangareddy, Telangana, India
Faiz Ahmed Khan

¹Department of Chemistry, Indian Institute of Technology Hyderabad, Kandi, Sangareddy, Telangana, India

Abstract

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Abstract

Racemic pimeforazine A (1) and B (2), neuroprotective compounds isolated from the weevil Pimelocerus perforatus, have attracted interest due to their potent biological activity. We report the first total synthesis of (±)-pimeforazine A and B, along with 16 structurally related analogues, starting from hydroxytyrosol. The key steps include the in-situ generation of a reactive electrophilic quinone intermediate from hydroxytyrosol, followed by a nucleophilic Michael addition with selected ortho-aminophenols. This one-pot transformation proceeds under mild aqueous conditions, utilizing molecular oxygen as the sole oxidant.

Keywords

Hydroxytyrosol - Biomimetic oxidation - Michael addition - Neuroprotective natural products - Quinone intermediates - Molecular oxygen oxidation

Full Text

References

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