Diastereoselective synthesis of novel alkaloid-like 1,2,3,3a,7b,12-hexahydroindeno[2′,1′:2,3]indeno[1,2-c]pyrroles

Abstract

2-Arylideneindan-1,3-diones readily undergo [3+2]-cycloaddition with N-methylazomethine ylide derived from sarcosine and formaldehyde to give 4′-aryl-1′-methylspiro[indene-2,3′-pyrrolidine]-1,3-diones, which were further cyclized in perchloric acid to (3aR*,7bR*,12aR*)-7b-hydroxy-2-methyl-2,3,3a,7b-tetrahydroindeno[2′,1′:2,3]indeno[1,2-c]pyrrol-12(1H)-ones in 33–100 % yields.