Synthesis of the tetracyclic core of tetrapetalone A enabled by a pyrrole reductive alkylation.
The tetracyclic framework of the tetrapetalone A aglycon has been secured through synthesis. A reductive pyrrole alkylation enables the formation of a key tetrasubstituted carbon stereocenter, and the tetramic acid portion of the molecule can be accessed through silicon or boronic ester conjugate addition to an ene-lactam.
Marcus
Andrew P
AP
Department of Chemistry, University of California, Berkeley, California 94720, USA.
Sarpong
Richmond
R
D000478:Alkylation; D001688:Biological Products / Q000737:chemistry; D006027:Glycosides / Q000138:chemical synthesis*; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D011758:Pyrroles / Q000737:chemistry*
D001688:Biological Products; D006027:Glycosides; D006576:Heterocyclic Compounds, 4 or More Rings; D011758:Pyrroles; C492598:tetrapetalone A