Domino Reactions for the Synthesis of Anthrapyran-2-ones and the Total Synthesis of the Natural Product (±)-BE-26554A

Domino Reactions for the Synthesis of Anthrapyran-2-ones and the Total Synthesis of the Natural Product (±)-BE-26554A

A domino alkyne addition/CO insertion/Nu acylation reaction to a series of novel anthrapyran-2-ones in good to excellent yields is described. In addition, an efficient synthetic sequence involving carbonylation, formation of a β-keto-sulfoxide, and cyclization is presented en route to the antibiotic...

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Veröffentlicht in:Organic letters 2013-09, Vol.15 (18), p.4834-4837
Hauptverfasser: Rixson, James E, Skelton, Brian W, Koutsantonis, George A, Gericke, Kersten M, Stewart, Scott G
Format: Artikel
Sprache:eng
Schlagworte:
Acylation
Alkynes - chemistry
Anthraquinones - chemical synthesis
Anthraquinones - chemistry
Anthraquinones - pharmacology
Anti-Bacterial Agents - chemical synthesis
Anti-Bacterial Agents - chemistry
Anti-Bacterial Agents - pharmacology
Antineoplastic Agents - chemical synthesis
Antineoplastic Agents - chemistry
Antineoplastic Agents - pharmacology
Biological Products - chemical synthesis
Biological Products - chemistry
Biological Products - pharmacology
Catalysis
Combinatorial Chemistry Techniques
Cyclization
Molecular Structure
Stereoisomerism
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Zusammenfassung:A domino alkyne addition/CO insertion/Nu acylation reaction to a series of novel anthrapyran-2-ones in good to excellent yields is described. In addition, an efficient synthetic sequence involving carbonylation, formation of a β-keto-sulfoxide, and cyclization is presented en route to the antibiotic and antitumor compound (±)-BE-26554A.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol402240v