Hydroxymethylation hydroxylation of 1,3-diarylpropene through a catalytic diastereoselective Prins reaction: cyclization logic and access to brazilin core

TL;DR

This paper describes a new chemical method to create specific compounds using a diastereoselective Prins reaction, which helps in building the core structure of a natural product called brazilin.

Contribution

The study introduces a novel catalytic diastereoselective Prins reaction for hydroxymethylation and hydroxylation of 1,3-diarylpropene.

Findings

The method produced various 1,3-dioxanes in 14–88% yields.

The synthetic intermediate 7h enabled the construction of the B/C rings in the brazilin core.

A sequential Friedel–Crafts/Ullmann-Ma reaction was more effective than the reverse order.

Abstract

A catalytic diastereoselective Prins reaction for hydroxymethylation and hydroxylation of 1,3-diarylpropene was successfully utilized to prepare various 1,3-dioxanes 7 in 14–88% yields. Take advantage of the synthetic intermediate 7h, the key B/C rings in brazilin core could be constructed by the sequential of Friedel–Crafts/Ullmann-Ma rather than Ullmann-Ma/Friedel–Crafts reactions.

The online version contains supplementary material available at 10.1007/s13659-024-00450-2.

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