Intramolecular formal oxa-[3 + 3] cycloaddition approach to the ABD system of phomactin A.
The ABD-ring of phomactin A was synthesized using an intramolecular formal oxa-[3 + 3] cycloaddion of an alpha,beta-unsaturated iminium salt tethered to a 1,3-diketone. This represents the first time that the 12-membered ring has been formed simultaneously with the 1-oxadecalin and should afford a facile route to the challenging structure of phomactin A. [reaction: see text]
Cole
Kevin P
KP
Department of Chemistry, University of Minnesota, 207 Pleasant Street SE, Minneapolis, MN 55455-0431, USA.
Hsung
Richard P
RP
D003500:Cyclization; D006575:Heterocyclic Compounds, 3-Ring / Q000138:chemical synthesis*; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis*; D008968:Molecular Conformation; D010972:Platelet Activating Factor / Q000037:antagonists & inhibitors; D013237:Stereoisomerism
D006575:Heterocyclic Compounds, 3-Ring; D006576:Heterocyclic Compounds, 4 or More Rings; D010972:Platelet Activating Factor; C413206:phomactin A