ScienceAsia 9 (1983): 073-079 |doi: 10.2306/scienceasia1513-1874.1983.09.073

PHOTOCHEMICAL SYNTHESIS OF A THEROSPERMIDINE

SURACHAI NIMGIRAWATH^a and WALTER C. TAYLOR^b

ABSTRACT: Irradiation of (Z)-1-(2-bromobenzylidene)-2-alkoxycarbonyl-5-methoxy-6, 7-methylenedioxy-1, 2, 3, 4-tetrahydroisoquinolines (6 and 7) afforded 6-alkoxycarbonyl-3-methoxy-1, 2-methylenedioxy-4, 5, 6, 7-tetrahydrodibenzo [ d e, g ] quinoline (8 and 9). Reduction of (8) or (9) with lithium aluminium hydride-aluminium chloride followed by oxidation with lead tetraacelate afforded atherospermidine (1) in low yield.

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a. Department of Chemistry, Faculty of Science, Silpakorn University, Nakorn Pathom 73000, Thailand.
b. Department of Organic Chemistry, the University of Sydney, N.S. W. 2006, Australia.

Received 7 March 1983