A concise total synthesis of (+/-)-bakkenolide A by means of an intramolecular Diels-Alder reaction.
(+/-)-Bakkenolide A was prepared in five steps from ethyl 4-benzyloxyacetoacetate by sequential alkylations with tiglyl bromide nd cis-5-bromo-1,3-pentadiene, followed by an intramolecular Diels-Alder reaction as the key step. The known 7-epibakkenolide A and novel 10-epi- and 7,10-diepibakkenolide A stereoisomers were obtained as minor byproducts.
Back
T G
TG
Department of Chemistry, University of Calgary, Alberta, Canada T2N 1N4. tgback@ucalgary.ca
Payne
J E
JE
D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D000972:Antineoplastic Agents, Phytogenic / Q000138:chemical synthesis*; D019659:Asteraceae / Q000737:chemistry; D007306:Insecticides / Q000138:chemical synthesis*; D012717:Sesquiterpenes; D013237:Stereoisomerism
D000972:Antineoplastic Agents, Phytogenic; D007306:Insecticides; D012717:Sesquiterpenes; D015107:4-Butyrolactone; C016257:bakkenolide A