Synthesis of Ring Size seco-Analogs of the Antitumor Antibiotic CC-1065 by Two Consecutive Transition Metal-Initiated Transformations

Novel seco-analogs of CC-1065 1 were synthesized from comercially available nitroaniline by reduction, bromination, bisulfonation and bisallylation followed by reaction with tert-butyllithium, zirconocene and iodine. The obtained quinoline 6 was then transformed into 17 and 18, which, upon treatment with Pd-0, led to 21 and 22, respectively. (C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.