Carboline I (R = CO2Me, R1 = H) was reduced by LiAlH4 to I (R = CH2OH, R1 = H) which was treated with MeCOCH:CH2 to give I (R = CH2OH, R1 = CH2CH2COMe). The latter compound was cyclized on treatment with AcCl under phase-transfer conditions to give the indoloquinolizine II. Intermediates in the cyclization were isolated and suggest the mechanism of the reaction.

Key words: STEREOSELECTIVITY, INDOLOQUINOLIZINE, CYCLIZATION, LITHIUM ALUMINIUM HYDRIDE, PORPHYRIN