Total Synthesis and Stereochemical Revision of the Chlorinated Sesquiterpene (±)‐Gomerone C

2012/11/14 by Nikolas Huwyler, Erick M. Carreira · 3 citations
Biochemistry, Genetics and Molecular Biology · Chemistry · #Chemical synthesis and alkaloids #Synthetic Organic Chemistry Methods #Traditional and Medicinal Uses of Annonaceae

paper · doi:10.1002/anie.201207203

openalex publication_date 2012/11/14 · openalex created_date 2025/10/10 · openalex updated_date 2026/07/29

Abstract

Revised: the total synthesis of gomerone C results in revision of the stereochemical assignment at C3. The synthetic strategy relies on a late-stage Conia-ene reaction, which efficiently forms the bicyclo[3.2.1]octane containing the bridgehead chloride and generates an exocyclic olefin, which can be used as a flexible handle for further elaboration. The two contiguous quaternary centers are installed by means of a Diels-Alder reaction.

Citations

• A New Method for Oxidation of Various Alcohols to the Corresponding Carbonyl Compounds by Using N-t-Butylbenzenesulfinimidoyl Chloride
• Gold(I)‐Catalyzed Cyclizations of Silyl Enol Ethers: Application to the Synthesis of (+)‐Lycopladine A
• The need for standardised broad scale bioassay testing: A case study using the red algaLaurencia rigida

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• Conia-ene reaction [wikipedia]

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