Catalytic Asymmetric Total Synthesis of (+)- and (−)-Paeoveitol via a Hetero-Diels–Alder Reaction

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• 作者：Tian-Ze Li ; Chang-An GengXiu-Juan Yin ; Tong-Hua Yang ; Xing-Long Chen ; Xiao-Yan Huang ; Yun-Bao Ma ; Xue-Mei Zhang ; Ji-Jun Chen
• 刊名：Organic Letters
• 出版年：2017
• 出版时间：February 3, 2017
• 年：2017
• 卷：19
• 期：3
• 页码：429-431
• 全文大小：304K
• ISSN：1523-7052

文摘

The first catalytic asymmetric total synthesis of (+)- and (−)-paeoveitol has been accomplished in 42% overall yield via a biomimetic hetero-Diels–Alder reaction. The chiral phosphoric acid catalyzed hetero-Diels–Alder reaction showed excellent diastereo- and enantioselectivity (>99:1 dr and 90% ee); two rings and three stereocenters were constructed in a single step to produce (−)-paeoveitol on a scale of 452 mg. This strategy enabled us to selectively synthesize both paeoveitol enantiomers from the same substrates by simply changing the enantiomer of the catalyst.