Synthesis of (+)-Muconin via Diastereoselective Oxypalladation

Synthesis of (+)-Muconin via Diastereoselective Oxypalladation

Synthesis of (+)-muconin isolated from Rollinia mucosa (Annonaceae) was achieved. Stereoselective construction of a tetrahydrofuran-terahydropyran (THF-THP) ring moiety was performed using diastereoselective oxypalladation in the presence of CuCl2. The cross-coupling reaction of the THF-THP moiety w...

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Veröffentlicht in:Journal of organic chemistry 2021-03, Vol.86 (6), p.4859-4866
Hauptverfasser: Sugimoto, Makoto, Nosho, Sayaka, Hikosaka, Gen, Hattori, Yasunao, Umezawa, Koji, Kawamura, Atsushi, Makabe, Hidefumi
Format: Artikel
Sprache:eng
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Zusammenfassung:Synthesis of (+)-muconin isolated from Rollinia mucosa (Annonaceae) was achieved. Stereoselective construction of a tetrahydrofuran-terahydropyran (THF-THP) ring moiety was performed using diastereoselective oxypalladation in the presence of CuCl2. The cross-coupling reaction of the THF-THP moiety with the γ-lactone portion followed by reduction of the enyne and removal of the protecting groups afforded (+)-muconin.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.0c02831