Work

Synthesis of Spirolactones from Carbonyls via Carboborylation of N‐ Sulfonylhydrazones with Alkoxycarbonylalkylboronic Acids

Year: 2025

Type: article

Abstract: A straightforward synthesis of spirolactones from carbonyls via N ‐tosylhydrazones is described. The process consists of a reaction between N ‐tosylhydrazones and ethoxycarbonylethylboronic acid or ethoxycarbonylpropylboronic acid, leading to spiro γ‐butyrolactones or δ‐valerolactones, respectively. The transformation takes place by carboborylation of the N ‐tosylhydrazone followed by oxidation of the homologated boronic acid that delivers a hydroxyester, which undergoes further lactonization to yield a spirocyclic lactone. Depending on the structure of the starting N ‐tosylhydrazone, thermal or photochemical protocols are applied for the key carboborylation reaction. The usefulness of the process is illustrated by the application in a variety of natural products and biologically relevant carbonyl‐containing molecules.

Source: Advanced Synthesis & Catalysis

DOI: 10.1002/adsc.202500170

Authors: Lucía López, Sara Filgueira, María‐Paz Cabal, Carlos Valdés

Institutions: Universidad de Oviedo, Instituto de Investigación Sanitaria del Principado de Asturias

Language: English

Topic: Organic Chemistry Synthesis Methods

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $4,650

Funders: Ministerio de Ciencia e Innovación, Agencia Estatal de Investigación