Synthesis of spirocyclopente-dione anthracene adduct, precursor of the cyclopentenone prostagladins via ring-closing metathesis reaction

A synthesis of the spirocyclopente-dione anthracene adduct, a precursor of the cyclopentenone prostaglandins has been reported. The synthesis involved a Diels-Alder reaction of anthracene and dimethyl fumarate to afford 3 followed by reduction, oxidation and esterification reactions to provide methyl ester anthracene adduct 8, which further converted to the the allylic alcohol (12). Then, Ring-Closing Metathesis (RCM) reaction afforded the cyclopentenol anthracene adduct, which after oxidation provided the spirocyclopente-dione anthracene adduct in good yields

Stereoselective synthesis of α-methylenecyclopentenones via a Diels-Alder/retro-Diels-Alder protocol

A new procedure for the stereoselective synthesis of cross-conjugated dienones is reported. This method makes use of the Diels–Alder adduct of anthracene and dimethyl fumarate, a precursor to a spirocyclopent-2-enone anthracene adduct as the key intermediate. The addition of propyllithium or octyllithium to the key intermediate followed by a retro-Diels–Alder reaction furnished α-methylenecyclopentenones bearing a γ-propyl or γ-octyl side chain, respectively, in moderate yields and as single geometric isomers

Synthesis of Spirocyclopente-Dione Anthracene Adduct, Precursor of the Cyclopentenone Prostagladins Via Ring-Closing Metathesis Reaction

Abstract: A synthesis of the spirocyclopente-dione anthracene adduct, a precursor of the cyclopentenone prostaglandins has been reported. The synthesis involved a Diels-Alder reaction of anthracene and dimethyl fumarate to afford 3 followed by reduction, oxidation and esterification reactions to provide methyl ester anthracene adduct 8, which further converted to the the allylic alcohol (12). Then, Ring-Closing Metathesis (RCM) reaction afforded the cyclopentenol anthracene adduct, which after oxidation provided the spirocyclopente-dione anthracene adduct in good yields

Stereoselective synthesis of α-methylenecyclopentenones via a Diels-Alder/retro-Diels-Alder protocol

A new procedure for the stereoselective synthesis of cross-conjugated dienones is reported. This method makes use of the Diels-Alder adduct of anthracene and dimethyl fumarate, a precursor to a spirocyclopent-2-enone anthracene adduct as the key intermed