Asymmetric Total Synthesis of Brasiliquinones B and C via Oxidative Cyclization of a Hydroquinone-Silyl Enol Ether Hybrid

The asymmetric total synthesis of angucycline antibiotics (S)-brasiliquinones B and C was accomplished. The benz­[a]­anthraquinone core was constructed via oxidative cyclization of a hydroquinone-silyl enol ether hybrid. The resultant pentacyclic acetal was converted to the silyl enol ether, which w...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 87; no. 18; pp. 12491 - 12497
Main Authors Miyake, Hiroki, Nakajima, Ryo, Kumamoto, Takuya
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 16.09.2022
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
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Summary:The asymmetric total synthesis of angucycline antibiotics (S)-brasiliquinones B and C was accomplished. The benz­[a]­anthraquinone core was constructed via oxidative cyclization of a hydroquinone-silyl enol ether hybrid. The resultant pentacyclic acetal was converted to the silyl enol ether, which was treated with Pd­(II)/O2 to afford brasiliquinone C, after multistep conversion including dehydrogenation, desilylation and deacetalization, and hydroquinone oxidation. The (S)-configuration of natural brasiliquinones was confirmed based on the stereochemical correlation with the synthetic products.
Bibliography:ObjectType-Article-1
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ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.2c01653