Asymmetric syntheses of epohelmins A and B by In-mediated allylation

作者：Liu, Yi-Wen; Han, Pan; Zhou, Wen; Mao, Zhuo-Ya; Si, Chang-Mei^*; Wei, Bang-Guo

来源：Organic and Biomolecular Chemistry, 2016, 14(45): 10714-10722.

DOI：10.1039/c6ob02212j

• TERT-BUTANESULFINYL IMINES
• LANOSTEROL SYNTHASE INHIBITORS
• FUNGAL STRAIN FKI-0929
• STEREOSELECTIVE-SYNTHESIS
• PYRROLIZIDINE ALKALOIDS
• DIVERGENT SYNTHESIS
• EFFICIENT SYNTHESIS
• SECONDARY ALCOHOLS
• VERSATILE APPROACH
• FLEXIBLE APPROACH

A diastereoselective new approach for the synthesis of trans-4-hydroxy-5-allyl-2-pyrrolidinone 9 has been developed through In-mediated allylation of alpha-chiral aldimine 8 with allyl bromide. The stereochemistry at the C-2 stereogenic center of 9 was controlled by both the alpha-OTBS substitution and the sulfinamide moiety. The utility of this asymmetric allylation is demonstrated by the asymmetric syntheses of epohelmins A (4) and B (10).

• 出版日期2016
• 单位复旦大学