Synlett

Synthesis of ansa-bridged macrocyclic lactams related to the antitumor antibiotic geldanamycin by ring closing metathesis

T Bach, A Lemarchand

Index: Bach, Thorsten; Lemarchand, Aude Synlett, 2002 , # 8 p. 1302 - 1304

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Citation Number: 14

Abstract

Abstract The α, β, γ, δ-unsaturated 2, 4, 5-trimethoxyanilides 8a-e which bear a terminal alkenyl side chain at the 3-position were prepared from 1, 2, 4-trimethoxybenzene (2) in four steps and 25-41% overall yield. Attempted ring closing metathesis reactions were successful in the presence of catalysts 9 for the substrates 8c-e and led to the products 10c-e (66-91% yield). Substrates 8a and 8b with a shorter alkenyl side chain did not cyclize.