Model studies toward the synthesis of the bioactive diterpenoid, harringtonolide.
In model studies towards the synthesis of harringtonolide, the construction of the tropone moiety via arene cyclopropanation was investigated. The installation of the lactone ring was accomplished by way of a Diels-Alder cycloaddition of various indenones and a-pyones. The incorporation of the key bridge methyl group and subsequent control of its stereochemistry is also outlined.
O'Sullivan
Timothy P
TP
Department of Chemistry, University College Cork, Cork, Ireland. tim.osullivan@ucc.ie
Zhang
Hongbin
H
Mander
Lewis N
LN
D018360:Crystallography, X-Ray; D003500:Cyclization; D004224:Diterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D006248:Harringtonines / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D013237:Stereoisomerism
D004224:Diterpenes; D006248:Harringtonines; C020752:hainanolide