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

Authors

Weerachai Phutdhawong, Kasetsart University
Gedsirin Eksinitkun, University of Wollongong
Stephen G. Pyne, University of WollongongFollow
Anthony C. Willis, Australian National University
Waya S. Phutdhawong, Silpakorn University

RIS ID

82922

Publication Details

Phutdhawong, W., Eksinitkun, G., Pyne, S. G., Willis, A. C. & Phutdhawong, W. S. (2013). Stereoselective synthesis of α-methylenecyclopentenones via a Diels-Alder/retro-Diels-Alder protocol. Tetrahedron, 69 (44), 9270-9276.

Abstract

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.