Study on Integrated Synthesis of Dimeric Pyranonaphthoquinones: Preparation of Versatile Synthetic Intermediate and Conversion into ent -Hemi-actinorhodin and ent -Hemi-γ-actinorhodin
Y. Ando, Mark M. Maturi, Taiju Hoshino, Nozomi Tanaka, Takahiro Sakai, K. Ohmori, Keisuke Suzuki
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引用次数: 0
Abstract
For developing general synthetic access toward dimeric pyrano-naphthoquinones including β-naphthocyclinone, actinorhodin and γ-actinorhodin, we report stereo-defined 6,9,10-trioxypyranonaphthalene as a versatile intermediate. Its robust preparation started from ethyl (S)-4-chloro-3-hydroxybutyrate. The pyranonaphthalene core was constructed by a Michael–Dieckmann sequence, and methylation using Me3Al and BF3·OEt2 established the required trans-structure in a scalable manner.. Conversion of this intermediate to ent-hemi-actinorhodin and to ent-hemi-γ-actinorhodin are also reported, in which the conditions for the oxidative lactonization were optimized.
期刊介绍:
SYNLETT is an international journal reporting research results and current trends in chemical synthesis in short personalized reviews and preliminary communications. It covers all fields of scientific endeavor that involve organic synthesis, including catalysis, organometallic, medicinal, biological, and photochemistry, but also related disciplines and offers the possibility to publish scientific primary data.