化学
芳基
烷基
药物化学
催化作用
多米诺骨牌
组合化学
有机化学
作者
Heesun Yu,Ryangha Lee,Hyoungsu Kim,Dongjoo Lee
出处
期刊:Organic Letters
[American Chemical Society]
日期:2021-01-25
卷期号:23 (3): 1135-1140
被引量:1
标识
DOI:10.1021/acs.orglett.1c00154
摘要
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.
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