We report the formal synthesis of angiogenesis inhibitor NM-3 (1) in six steps from either of the 2, 4-dimethoxyhalobenzenes 13a, b or 3, 5-dimethoxychlorobenzene (13c). The first key reaction is the regiospecific alkylation/rearrangement between the aryne derived from 13a-c with sodium diethylmalonate in THF to produce diester 11, which after hydrolysis and cyclization affords homophthalic anhydride 3. The second is the reaction of anhydride 3 ...
