The Total Synthesis of Racemic Teucvin and 12‐<i>epi</i>‐Teucvin

A novel strategy for the synthesis of cis-decalins by an ytterbium-catalyzed asymmetric inverse-electron-demand Diels-Alder reaction of 2-pyrones and silyl cyclohexadienol ethers is reported here. A broad range of synthetically important cis-decalin derivatives with multiple contiguous stereogenic centers and functionalities are obtained in good yields and stereoselectivities. A full set of diastereomeric substituted cis-decalin motifs are readily accessible by tuning the absolute configurations of substituted silyl cyclohexadienol ethers (R or S) as well as the ligands (R or S). The synthetic potential is showcased by the enantioselective total synthesis of 4-amorphen-11-ol, and further demonstrated by the first total synthesis of cis-crotonin. Scheme 1. Enantioselective synthesis of cis-decalin motifs by inverseelectron-demand Diels-Alder reaction of 2-pyrones.

show abstract

Asymmetric Allylic Alkylation of Cyclic Vinylogous Esters and Thioesters by Pd‐Catalyzed Decarboxylation of Enol Carbonate and β‐Ketoester Substrates

Trost

Bream

2006

Angew Chem Int Ed

171

View full text Add to dashboard Cite

Excellent yields and enantioselectivities were achieved for the palladium‐catalyzed asymmetric allylic alkylation of vinylogous thioesters. The close‐to‐neutral reaction conditions ensure that this reaction can tolerate a wide range of functionalities. Furthermore, this approach provides a convenient protocol for the synthesis of synthetically important α,α‐ and γ,γ‐disubstituted cycloalkenones.

show abstract

scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.

Contact Info

customersupport@researchsolutions.com

10624 S. Eastern Ave., Ste. A-614

Henderson, NV 89052, USA

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Blog Terms and Conditions API Terms Privacy Policy Contact Cookie Preferences Do Not Sell or Share My Personal Information

Made with 💙 for researchers

Part of the Research Solutions Family.

The Total Synthesis of Racemic Teucvin and 12‐epi‐Teucvin

Abstract: Vollständige Seiten‐, Stereo‐ und Regioselektivität bei der Diels‐Alder‐Reaktion von 1 mit 2 legte den Grundstein zu den ersten Totalsynthesen der 19‐Norclerodan‐Diterpenoide Teucvin und 12‐epi‐Teucvin in racemischer Form.

Cited by 5 publications

References 14 publications

Asymmetric Allylic Alkylation of Cyclic Vinylogous Esters and Thioesters by Pd‐Catalyzed Decarboxylation of Enol Carbonate and β‐Ketoester Substrates

Asymmetric Allylic Alkylation of Cyclic Vinylogous Esters and Thioesters by Pd‐Catalyzed Decarboxylation of Enol Carbonate and β‐Ketoester Substrates

Enantioselective Synthesis of cis‐Decalin Derivatives by the Inverse‐Electron‐Demand Diels–Alder Reaction of 2‐Pyrones

Asymmetric Allylic Alkylation of Cyclic Vinylogous Esters and Thioesters by Pd‐Catalyzed Decarboxylation of Enol Carbonate and β‐Ketoester Substrates

Contact Info

Product

Resources

About