Convergent enantioselective synthesis of the tricyclic core of phomactin A.
[reaction: see text] The tricyclic core of phomactin A was synthesized from 6,6-dimethyl-2-cyclohexen-1-one. Key reactions include the addition of a cyclohexenyllithium reagent to an epoxyaldehyde and a regioselective intramolecular epoxide opening to install the oxadecalin core.
Mohr
Peter J
PJ
Department of Chemistry and Biochemistry, University of Colorado, Boulder, Colorado 80309-0215, USA.
Halcomb
Randall L
RL
D001203:Ascomycota / Q000737:chemistry*; D004852:Epoxy Compounds / Q000737:chemistry; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D010972:Platelet Activating Factor / Q000037:antagonists & inhibitors*
D004852:Epoxy Compounds; D006576:Heterocyclic Compounds, 4 or More Rings; D007202:Indicators and Reagents; D010972:Platelet Activating Factor; C413206:phomactin A