An alternative synthesis of the breast cancer drug fulvestrant (Faslodex®): catalyst control over C-C bond formation

Diego Caprioglio; Stephen P Fletcher

doi:10.1039/c5cc05805h

An alternative synthesis of the breast cancer drug fulvestrant (Faslodex®): catalyst control over C-C bond formation

Chem Commun (Camb). 2015 Oct 14;51(80):14866-8. doi: 10.1039/c5cc05805h.

Authors

Diego Caprioglio¹, Stephen P Fletcher

Affiliation

¹ Department of Chemistry, Chemistry Research Laboratory, University of Oxford, 12 Mansfield road, OX1 3TA, UK. stephen.fletcher@chem.ox.ac.uk.

PMID: 26300021
DOI: 10.1039/c5cc05805h

Abstract

Fulvestrant (Faslodex®) was synthesized in four steps (35% overall yield) from 6-dehydronandrolone acetate. Catalyst controlled, room temperature, diastereoselective 1,6-addition of the zirconocene derived from commercially available 9-bromonon-1-ene was used in the key C-C bond forming step.

MeSH terms

Antineoplastic Agents / chemistry
Antineoplastic Agents / pharmacology*
Antineoplastic Agents / therapeutic use
Breast Neoplasms / drug therapy
Catalysis
Estradiol / analogs & derivatives*
Estradiol / chemistry
Estradiol / pharmacology
Estradiol / therapeutic use
Fulvestrant

Substances

Antineoplastic Agents
Fulvestrant
Estradiol