Issue 56, 2024

9-Step synthesis of (−)-larikaempferic acid methyl ester enabled by skeletal rearrangement

Abstract

We report here a concise synthesis of the anti-tumor-promoting (−)-larikaempferic acid methyl ester, a novel and rearranged abietane-type diterpene natural product containing a unique tetracyclic skeleton with a trans-hydrindane, an oxabicyclo[3.2.1]octane, and six stereogenic centers. Our synthesis starts with the cheap and abundant abietic acid and features an oxidative C–C bond cleavage followed by a transannular aldol reaction to skeletally rearrange the 6–6–6 tricyclic carbon skeleton of abietic acid to the desired 6–5–7 tricyclic carbon skeleton and an intramolecular oxa-Michael addition to form the oxa bridge. This skeletal rearrangement strategy enabled us to synthesize (−)-larikaempferic acid methyl ester in 9 steps.

Graphical abstract: 9-Step synthesis of (−)-larikaempferic acid methyl ester enabled by skeletal rearrangement

Supplementary files

Article information

Article type
Communication
Submitted
30 mrt 2024
Accepted
07 mei 2024
First published
09 mei 2024
This article is Open Access
Creative Commons BY license

Chem. Commun., 2024,60, 7164-7167

9-Step synthesis of (−)-larikaempferic acid methyl ester enabled by skeletal rearrangement

M. E. Rivera, L. Li, A. Kolisetti, N. Chi and M. Dai, Chem. Commun., 2024, 60, 7164 DOI: 10.1039/D4CC01462F

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