Purification as described in part A gave hemiketal 42,288 mg (0.95 mmol, 60% yield).trans-6- 3,4,4a,5,6,6a,benzopyrano[4,3,2-ef]isoqumoline 3,4,4a,5,6,6a,benzopyrano[4,3^-e/]isoquinoline (45). Potassium tert-butoxide (1.5 g, 12.5 mmol) containing residual tert-butyl alcohol was added to degassed DMF (30 mL) under argon, and the suspension was degassed with argon for 1 h. EtSH (1.5 mL, 1.26 g, 20.25 mmol) was then added to provide a ca. 0.68 M solution of EtSK in DMF. Amino ketone 38 (60 mg, 0.2 mmol) was added to the EtSK/DMF solution (2.5 mL, 1.7 mmol) and heated at 100 °C (bT) under argon for 8 h. The solution was allowed to cool and after 12 h was evaporated, the residue was dissolved in 0.6 M aqueous NaOH (20 mL), the solution was extracted with CH2C12 (2 X 10 mL), and the combined organic phases were dried and evaporated to an oil which crystallized from PhH to give 44: 25 mg (0.087 mmol, 43%); mp 125-140 °C; IR (CHC13) 3330, 3280 cm"1 2; NMR (60 MHz) 6.90 (m, 3 H), 6.55 (br s), 4.87 (s, 3 H), 2.49 (s, 3 ), 3.5-1.2 (m); mass spectrum, m/z (relative intensity) 289 (19), 218 (13), 45 (100).