Domino reactions for the synthesis of anthrapyran-2-ones and the total synthesis of the natural product (±)-BE-26554A

James E Rixson; Brian W Skelton; George A Koutsantonis; Kersten M Gericke; Scott G Stewart

doi:10.1021/ol402240v

Domino reactions for the synthesis of anthrapyran-2-ones and the total synthesis of the natural product (±)-BE-26554A

Org Lett. 2013 Sep 20;15(18):4834-7. doi: 10.1021/ol402240v. Epub 2013 Sep 5.

Authors

James E Rixson¹, Brian W Skelton, George A Koutsantonis, Kersten M Gericke, Scott G Stewart

Affiliation

¹ The School of Chemistry and Biochemistry, and Centre for Microscopy, Characterisation and Analysis, The University of Western Australia , Crawley, WA 6009, Australia, and Bayer Pharma AG , Medicinal Chemistry, 42096 Wuppertal, Germany.

PMID: 24006880
DOI: 10.1021/ol402240v

Abstract

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.

MeSH terms

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

Substances

Alkynes
Anthraquinones
Anti-Bacterial Agents
Antineoplastic Agents
BE-26554A
Biological Products