Total synthesis of the antitumor antibiotic (±)‐fredericamycin A by a linear approach

Y Kita, K Iio, K Kawaguchi, N Fukuda… - … A European Journal, 2000 - Wiley Online Library
Y Kita, K Iio, K Kawaguchi, N Fukuda, Y Takeda, H Ueno, R Okunaka, K Higuchi, T Tsujino…
Chemistry–A European Journal, 2000Wiley Online Library
A linear approach to the total synthesis of racemic fredericamycin A (1) through the oxidative
intramolecular [4+ 2] cycloaddition of a (phenylthio) acetylene–cobalt complex is described,
which is applicable for the asymmetric total synthesis of naturally occuring 1. The highlight of
this work is the aromatic Pummerer‐type reaction with 1‐ethoxyvinyl chloroacetate, which
effects the introduction of the oxygen functional group to the internal B‐ring of the highly
functionalized, congested polyaromatic ABC‐ring moiety.
Abstract
A linear approach to the total synthesis of racemic fredericamycin A (1) through the oxidative intramolecular [4+2] cycloaddition of a (phenylthio)acetylene–cobalt complex is described, which is applicable for the asymmetric total synthesis of naturally occuring 1. The highlight of this work is the aromatic Pummerer‐type reaction with 1‐ethoxyvinyl chloroacetate, which effects the introduction of the oxygen functional group to the internal B‐ring of the highly functionalized, congested polyaromatic ABC‐ring moiety.
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