Formal synthesis of angiogenesis inhibitor NM-3

WE Bauta, DP Lovett, WR Cantrell…

Index: Bauta, William E.; Lovett, Dennis P.; Cantrell Jr., William R.; Burke, Brian D. Journal of Organic Chemistry, 2003 , vol. 68, # 15 p. 5967 - 5973

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Citation Number: 50

Abstract

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 ...