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Title: Bioinspired Diastereoconvergent Synthesis of the Tricyclic Core of Palodesangrens via Diels-Alder Reaction, LiAlH<inf>4</inf>-Mediated Isomerization, and Acid-Mediated Cyclization
Authors: Poramate Songthammawat
Sirilak Wangngae
Koki Matsumoto
Chuthamat Duangkamol
Somsak Ruchirawat
Poonsakdi Ploypradith
Chulabhorn Research Institute
Thailand Ministry of Education
Mahidol University
Chulabhorn Royal Academy
Keywords: Chemistry
Issue Date: 4-May-2018
Citation: Journal of Organic Chemistry. Vol.83, No.9 (2018), 5225-5241
Abstract: © 2018 American Chemical Society. The cyclohexene moiety of the tricyclic 6,7-diaryl-tetrahydro-6H-benzo[c]chromene core of palodesangrens could be assembled in a biomimetic and step-economical fashion by the Diels-Alder reaction between the electron-rich (E)-1,3-butadienylarenes as the diene and the electron-deficient chalcones as the dienophile. During the reduction of ketone to the corresponding alcohol by LiAlH4, the mixture of endo and exo isomers underwent a novel diastereoconvergent LiAlH4-mediated isomerization to install the desired stereochemistry at C10a. Subsequent pyran ring closure under acidic conditions installed the stereochemistry at the remaining C6. Overall, the tricyclic core of palodesangrens could be prepared in three steps and up to 38% yield.
ISSN: 15206904
Appears in Collections:Scopus 2018

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