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Synthesis of Ring Size seco ‐Analogs of the Antitumor Antibiotic CC‐1065 by Two Consecutive Transition Metal‐Initiated Transformations
Author(s) -
Tietze Lutz F.,
Looft Jan,
Feuerstein Tim
Publication year - 2003
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200300077
Subject(s) - chemistry , quinoline , halogenation , transition metal , ring (chemistry) , iodine , stereochemistry , medicinal chemistry , combinatorial chemistry , organic chemistry , catalysis
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. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)