TY - JOUR
T1 - Stereoselective synthesis of α-methylenecyclopentenones via a Diels-Alder/retro-Diels-Alder protocol
AU - Phutdhawong, Weerachai
AU - Eksinitkun, Gedsirin
AU - Pyne, Stephen G.
AU - Willis, Anthony C.
AU - Phutdhawong, Waya S.
PY - 2013/11/4
Y1 - 2013/11/4
N2 - 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.
AB - 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.
KW - Anthracene
KW - Diels-Alder/retro-Diels-Alder
KW - Stereoselective synthesis
KW - α-Methylenecyclopentenones
UR - http://www.scopus.com/inward/record.url?scp=84884416286&partnerID=8YFLogxK
U2 - 10.1016/j.tet.2013.08.046
DO - 10.1016/j.tet.2013.08.046
M3 - Article
SN - 0040-4020
VL - 69
SP - 9270
EP - 9276
JO - Tetrahedron
JF - Tetrahedron
IS - 44
ER -