Tetrahedron Letters p. 1149 - 1152 (1999)
Update date:2022-08-04
Topics:
Ishibashi
Inomata
Ohba
Ikeda
The treatment of easmide 15, having an (E)-4-ethoxycarbonyl-3-butenyl group on the nitrogen atrom, with Bu3SnH-AIBN in boiling benzene, afforded a 1.2:1 mixture of two benzo[a]quinolizidine stereoisomers 16 and 17 as a result of cascade radical cyclization. A similar treatment of the (Z)-4- ethoxycarbonyl-3-butenyl congener 19 gave 16 and 17 in a ratio of 3.4:1. The high stereoselectivity (16:17=37:1) from 19 was obtained using Et3B as the initiatior at -78 °C in toluene.
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