Publication:
Bioinspired Diastereoconvergent Synthesis of the Tricyclic Core of Palodesangrens via Diels-Alder Reaction, LiAlH<inf>4</inf>-Mediated Isomerization, and Acid-Mediated Cyclization

Issued Date

2018-05-04

Resource Type

Article

ISSN

15206904
00223263

DOI

10.1021/acs.joc.8b00668

Other identifier(s)

2-s2.0-85046284982

Rights

Mahidol University

Rights Holder(s)

SCOPUS

Bibliographic Citation

Journal of Organic Chemistry. Vol.83, No.9 (2018), 5225-5241

Suggested Citation

Poramate Songthammawat, Sirilak Wangngae, Koki Matsumoto, Chuthamat Duangkamol, Somsak Ruchirawat, Poonsakdi Ploypradith Bioinspired Diastereoconvergent Synthesis of the Tricyclic Core of Palodesangrens via Diels-Alder Reaction, LiAlH<inf>4</inf>-Mediated Isomerization, and Acid-Mediated Cyclization. Journal of Organic Chemistry. Vol.83, No.9 (2018), 5225-5241. doi:10.1021/acs.joc.8b00668 Retrieved from: https://repository.li.mahidol.ac.th/handle/20.500.14594/45495

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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

Author(s)

Poramate Songthammawat
 Sirilak Wangngae
 Koki Matsumoto
 Chuthamat Duangkamol
 Somsak Ruchirawat
 Poonsakdi Ploypradith

Other Contributor(s)

Chulabhorn Research Institute
 Thailand Ministry of Education
 Mahidol University
 Chulabhorn Royal Academy

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.

Keyword(s)

Chemistry

Availability

URI

https://repository.li.mahidol.ac.th/handle/20.500.14594/45495

Collections

Scopus 2018