Jumreang TummatornPrapas KhorphuengAmorn PetsomNongnuch MuangsinNarongsak ChaichitSophon RoengsumranMahidol UniversityMahanakorn University of TechnologyThammasat University2018-08-242018-08-242007-11-26Tetrahedron. Vol.63, No.48 (2007), 11878-11885004040202-s2.0-35348843387https://repository.li.mahidol.ac.th/handle/20.500.14594/24081Synthesis 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.Mahidol UniversityBiochemistry, Genetics and Molecular BiologyChemistryPharmacology, Toxicology and PharmaceuticsArticleSCOPUS10.1016/j.tet.2007.09.032