First Total Syntheses of Tetracenomycins C and X

The first total syntheses of tetracenomycins C and X were achieved, featuring 1) preparation of a hexasubstituted naphthonitrile oxide by successive benzyne cycloadditions and an oxidative ring‐opening reaction; 2) a novel ortho‐quinone mono‐acetal as the A‐ring unit; 3) construction of three contig...

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Published inAngewandte Chemie Vol. 129; no. 41; pp. 12782 - 12787
Main Authors Sato, Shogo, Sakata, Keiichiro, Hashimoto, Yoshimitsu, Takikawa, Hiroshi, Suzuki, Keisuke
Format Journal Article
LanguageEnglish
Published Weinheim Wiley Subscription Services, Inc 02.10.2017
Subjects
Antibiotika
Arine
Asymmetrische Synthesen
Benzoin
Chemistry
Isoxazole
Nitriloxide
Oxidation
Quinones
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Summary:The first total syntheses of tetracenomycins C and X were achieved, featuring 1) preparation of a hexasubstituted naphthonitrile oxide by successive benzyne cycloadditions and an oxidative ring‐opening reaction; 2) a novel ortho‐quinone mono‐acetal as the A‐ring unit; 3) construction of three contiguous stereogenic centers by an asymmetric benzoin cyclization, an isoxazole oxidation, and a stereoselective reduction. Tetracenomycin C und X wurden in Totalsynthesen über hexasubstituierte Naphthonitriloxide und ein ortho‐Chinon‐Monoacetal als Zwischenstufen hergestellt. Durch eine asymmetrische Benzoin‐Cyclisierung wurden drei benachbarte Stereozentren eingeführt. Weitere Schlüsselschritte waren eine Isoxazol‐Oxidation und eine stereoselektive Reduktion.
ISSN:0044-8249
1521-3757
DOI:10.1002/ange.201707099