Publication:
Convenient synthetic route to a dehydrorotenoid via selective intramolecular aldol condensation of 1,2-diaryl diketone

Issued Date

2007-11-26

Resource Type

Article

ISSN

00404020

DOI

10.1016/j.tet.2007.09.032

Other identifier(s)

2-s2.0-35348843387

Rights

Mahidol University

Rights Holder(s)

SCOPUS

Bibliographic Citation

Tetrahedron. Vol.63, No.48 (2007), 11878-11885

Suggested Citation

Jumreang Tummatorn, Prapas Khorphueng, Amorn Petsom, Nongnuch Muangsin, Narongsak Chaichit, Sophon Roengsumran Convenient synthetic route to a dehydrorotenoid via selective intramolecular aldol condensation of 1,2-diaryl diketone. Tetrahedron. Vol.63, No.48 (2007), 11878-11885. doi:10.1016/j.tet.2007.09.032 Retrieved from: https://repository.li.mahidol.ac.th/handle/20.500.14594/24081

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Title

Convenient synthetic route to a dehydrorotenoid via selective intramolecular aldol condensation of 1,2-diaryl diketone

Author(s)

Jumreang Tummatorn
 Prapas Khorphueng
 Amorn Petsom
 Nongnuch Muangsin
 Narongsak Chaichit
 Sophon Roengsumran

Other Contributor(s)

Mahidol University
 Mahanakorn University of Technology
 Thammasat University

Abstract

Synthesis of dehydrorotenoid (1) was successfully achieved via an intramolecular aldol reaction of the corresponding 1,2-diaryl diketone intermediate. The 1,2-diaryl diketone was prepared using a ruthenium-catalyzed oxidation of the corresponding substituted diaryl acetylene. Treatment of this 1,2-diketone with l-proline induced a selective intramolecular aldol condensation reaction, forming the desired benzopyranone over the alternative benzofuran. Deprotection, cyclization, and dehydration gave the target compound in good overall yield. © 2007 Elsevier Ltd. All rights reserved.

Keyword(s)

Biochemistry, Genetics and Molecular Biology
 Chemistry
 Pharmacology, Toxicology and Pharmaceutics

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URI

https://repository.li.mahidol.ac.th/handle/20.500.14594/24081

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Scopus 2006-2010