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

Authors

Gedsirin Eksinitkun, University of Wollongong
Stephen G. Pyne, University of WollongongFollow
Waya S. Phutdhawong, Silpakorn University
Weerachai Phutdhawong, Kasetsart University

RIS ID

89535

Publication Details

Eksinitkun, G., Pyne, S. G., Phutdhawong, W. S. & Phutdhawong, W. (2013). Synthesis of spirocyclopente-dione anthracene adduct, precursor of the cyclopentenone prostagladins via ring-closing metathesis reaction. Chemical Science Transactions, 2 (4), 1496-1502.

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.