(10Z)-tricyclo[10.4.0.04,9]hexadeca-1(16),4,6,8,10,12,14-heptaen-2-one

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 5-oxo-dibenzo[a,e]cyclooctene (1 g, Example 1, step E) in ethanol (40 ml) was added hydroxylamine hydrochloride (0.316 g) and pyridine (0.404 ml). This mixture was heated to reflux for 8hr, cooled to room temperature and evaporated to dryness. To the residue was added ethyl acetate (100 ml). water (100 ml),then sodium hydroxide (1M) until pH 10. The aqueous layer was extracted with ethyl acetate (200 ml), the combined organic layers were washed with water (100 ml), brine (100 ml) then dried and evaporated to yield the crude product. Recrystallisation from ethyl acetate-hexane gave pure 5-hydroxyimino-dibenzo[a,e]cyclooctene (0.72 g, m.p. 191°-192°C. This mixture was heated to reflux for 8hr evaporated to dryness To the residue was added ethyl acetate (100 ml) The aqueous layer was extracted with ethyl acetate (200 ml) the combined organic layers were washed with water (100 ml), brine (100 ml) then dried evaporated to yield the crude product Recrystallisation from ethyl acetate-hexane

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred solution of 5-oxo-dibenzo[a,e]cyclooctene (10.0 g) in dry diethyl ether at 0° C. under nitrogen, was added over 5 minutes, through a canula, a solution of methyl lithium (40 ml of a 1.4M solution in diethyl ether). After a further 10 minutes stirring water (40 ml) was added cautiously and the separated aqueous layer discarded. The organic layer was washed with water. then dried and evaporated. Crystallisation from diethyl ether/hexane gave the pure alcohol (6.2 g), mp 108°-109° C. was added cautiously The organic layer was washed with water then dried evaporated Crystallisation from diethyl ether/hexane

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of oxalyl chloride (5 ml) in dry dichloromethane (75 ml) at -78° C. under nitrogen was added, dropwise. dimethyl sulphoxide (8.75 ml), and the solution stirred at -78° C. for 15 minutes. A solution of 5-hydroxy-dibenzo[a,e]cyclooctene (11.1 g) in dichloromethane (75 ml) was added over 5 minutes at -78° C. and the solution stirred for 15 minutes, then triethylamine (30 ml) was added and the mixture allowed to warm to room temperature. The mixture was washed with water (100 ml), 1N hydrochloric acid (50 ml) water (100 ml), brine (50 ml) then dried and evaporated to give the crude ketone which was recrystallised from ethyl alcohol/hexane (10.0 g), mp 112°-6 ° C. The mixture was washed with water (100 ml), 1N hydrochloric acid (50 ml) water (100 ml), brine (50 ml) then dried evaporated