Synthesis of 5,5,6-Fused Tricyclic Lactones: Stereocontrol of Three Consecutive Stereocenters

TL;DR

This paper describes a new method to create complex tricyclic lactones with precise stereochemistry using a series of chemical reactions.

Contribution

The novel contribution is a diastereoselective synthesis of tricyclic γ-lactones with three consecutive stereocenters using palladium-catalyzed reactions.

Findings

A palladium-catalyzed tandem Heck/Suzuki reaction was used to synthesize strained tricyclic γ-lactones.

The method enables stereocontrolled synthesis from simple, biomass-derived starting materials.

The approach provides access to complex molecular scaffolds relevant in synthetic and medicinal chemistry.

Abstract

We report a new,
highly diastereoselective method for the synthesis
of strained 5,5,6-fused tricyclic γ-lactones via a palladium-catalyzed
tandem Heck/Suzuki cross-coupling reaction, followed by epoxidation
and lactone-forming epoxide opening. Using this sequence, we prepared
tricyclic γ-lactones with three consecutive stereocenters from
simple, readily available starting materials, including one derived
from enantiomerically pure biomass-based levoglucosenone. Our method
provides a stereocontrolled approach to complex scaffolds of potential
relevance in synthetic and medicinal chemistry.

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