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Enantioselective Total Synthesis of Lycoposerramine‑Z Using Chiral Phosphoric Acid Catalyzed Intramolecular Michael Addition

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journal contribution
posted on 12.02.2016, 00:00 by Lan-De Zhang, Lin-Rui Zhong, Jie Xi, Xiao-Liang Yang, Zhu-Jun Yao
A new enantioselective total synthesis of phlegmarine-type Lycopodium alkaloid lycoposerramine-Z (1) has been accomplished, using one-pot chemoselective sequential additions of two different Grignard reagents to the bis-Weinreb-amide intermediate and an efficient construction of the fully fuctionalized cyclohexanone intermediate with a chiral phosphoric acid catalyzed enantioselective intramolecular Michael addition.