A Concise Enantioselective Formal Synthesis of the Second-Generation Oral Contraceptive Levonorgestrel

Dražen Pavlović; Daniel F A R Dourado; Andrew S. Rowan; Gareth Brown; Darren W. Gray; Jenny Spratt; Alexandra T P Carvalho; Jill M. Caswell; Derek J. Quinn; Sergei Maciuk; Fernando Tur; Stefan Mix; Thomas S. Moody

doi:10.26434/chemrxiv.15000108/v1

A Concise Enantioselective Formal Synthesis of the Second-Generation Oral Contraceptive Levonorgestrel

ChemRxiv 2026 Preprint Open access

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Authors: Dražen Pavlović, Daniel F A R Dourado, Andrew S. Rowan, Gareth Brown, Darren W. Gray, Jenny Spratt, Alexandra T P Carvalho, Jill M. Caswell, Derek J. Quinn, Sergei Maciuk, Fernando Tur, Stefan Mix

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Thomas S. Moody

DOI: 10.26434/chemrxiv.15000108/v1

Cited by: 1

Abstract

A concise formal synthesis of levonorgestrel (LNG) precursor, a natural 18a-homoestrone, 13-ethyl-3methoxy-gona-2,5(10)-dien-17-one (11) is described, in which the steroid core of LNG is formed by enantioselective CRED bioreduction of prochiral secodione 4 followed by Torgov cyclization as the key steps.

Fields of Study & Subjects

Steroid Chemistry and Biochemistry Estrogen and related hormone effects Phytochemistry and Bioactive Compounds

Publication details

Journal / source: ChemRxiv
Publisher: American Chemical Society (ACS)
Publication date: 16 February 2026
Document type: Preprint