Details

Autor(en) / Beteiligte

• Yu, Heesun
• Lee, Ryangha
• Kim, Hyoungsu
• Lee, Dongjoo

Titel

Diastereoselective Construction of trans-2-Alkyl-6-aryl-3,6-dihydro‑2H‑pyrans via Dehydrogenative Cycloetherification Promoted by DDQ

Ist Teil von

• Organic letters, 2021-02, Vol.23 (3), p.1135-1140

Ort / Verlag

American Chemical Society

Erscheinungsjahr

2021

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• A diastereoselective synthesis of trans-2-alkyl-6-aryl-3,6-dihydro-2H-pyrans has been described. Dehydrogenative cycloetherification of (E)-(±)-1-aryl-5-hydroxy-1-alkenes promoted by DDQ proceeded cleanly via 6-endo cyclization to afford trans-2-alkyl-6-aryl-3,6-dihydro-2H-pyrans (32 examples) in good yield (up to 89%) and with moderate to excellent diastereoselectivity (up to 99:1). The synthetic utility of the method was illustrated by the second total synthesis of (±)-(2R,6S)-3,4-dehydro-1,7-bis­(4-hydroxy phenyl)-4′-de-O-methyl centrolobine and a total synthesis of (±)-centrolobine.