The Chemical Constituents of Australian Flindersia Species. XI. The Structures of Maculosidine and Maculosine, two Alkaloids from F. maculosa Lindl

Abstract

Maculosidine has the structure I, previously suggested. By degradation it is converted to 6,8-dimethoxy-3-ethyl-4-hydroxy-2-quinolone, identified by synthesis. Maculosine, which has formula C17H1706N and the typical ultraviolet spectrum of a furoquinoline, is oxidized by periodate to a substance which is degraded to the known 3-ethyl-4-hydroxy-6,7-methylenedioxy-2-quinolone. This evidence leads to the assignment of IV as its structure.