Issue 27, 2025

Asymmetric total syntheses of passifetilactones A, C, E and 4-epi-passifetilactone B

Abstract

This paper describes the efficient asymmetric total syntheses of passifetilactones A, C, E and 4-epi-passifetilactone B. Keck allylation and ring-closing metathesis (RCM) have been employed as the key steps in the synthesis of passifetilactones A and C, while Sharpless kinetic resolution (SKR) and RCM have been utilized in the syntheses of passifetilactone E and 4-epi-passifetilactone B. The total syntheses of passifetilactones A, C, E and 4-epi-passifetilactone B required 8, 4, 8 and 10 steps with good overall yields of 37.4%, 60%, 10.2% and 3.5%, respectively. The synthesis efforts also established the absolute structures of these molecules.

Graphical abstract: Asymmetric total syntheses of passifetilactones A, C, E and 4-epi-passifetilactone B

Supplementary files

Article information

Article type
Paper
Submitted
08 mag 2025
Accepted
18 giu 2025
First published
19 giu 2025

Org. Biomol. Chem., 2025,23, 6637-6643

Asymmetric total syntheses of passifetilactones A, C, E and 4-epi-passifetilactone B

S. B. Khandekar, N. R. Barnala and R. A. Fernandes, Org. Biomol. Chem., 2025, 23, 6637 DOI: 10.1039/D5OB00756A

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