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A regioselective diels-alder synthesis of ellipticine

1990; Elsevier BV; Volume: 31; Issue: 8 Linguagem: Inglês

10.1016/s0040-4039(00)88731-6

1873-3581

Deborah A. Davis, Gordon W. Gribble,

Synthesis and bioactivity of alkaloids

The trimethylsilyl trifluoromethanesulfonate accelerated Diels-Alder reaction between 1,3-dimethyl-4-(phenylsulfonyl)-4H-furo[3,4-b]indole (3) and 5,6-dihydropyridones (10) shows high regioselectivity, yielding carbazole 11 upon hydrolytic workup. Carbazole 11b has been successfully converted to the pyridocarbazole alkaloid ellipticine (1).