Work

A Straightforward Synthesis of Benzestrol by Matteson Homologation Using Chiral Benzyl Carbamates

Year: 2026

Type: article

Abstract: A straightforward and highly stereoselective synthesis of the non‐steroidal estrogen benzestrol is described based on Matteson homologations. Starting from a chiral arylboronic ester two classical Matteson reactions allow the introduction of two stereogenic centers, while the third one is transferred from a chiral benzyl carbamate under retention. Protodeboration and deprotection provide benzestrol in only 6 steps and an overall yield of 30%.

Source: European Journal of Organic Chemistry

DOI: 10.1002/ejoc.70791

Authors: Max Benjamin Becker, Uli Kazmaier

Institution: Saarland University

Language: English

Topic: Asymmetric Synthesis and Catalysis

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $4,330

Funder: Deutsche Forschungsgemeinschaft