American Chemical Society
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Total Synthesis of (−)-Graminin A Based on Asymmetric Cyclization Carbonylation of Propargyl Acetate

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journal contribution
posted on 2019-12-12, 15:43 authored by Yoichi Ito, Taichi Kusakabe, Yogesh Daulat Dhage, Keisuke Takahashi, Ken Sakata, Hiroaki Sasai, Keisuke Kato
The first total synthesis of (−)-graminin A is described. Key features of our synthetic approach involve a palladium-catalyzed asymmetric cyclization carbonylation of prochiral propargylic acetate, conversion of the orthoester product into methyl 4-oxo-3-furancarboxylate, and copper complex-mediated aldol condensation of (+)-gregatin B bearing a diene moiety. A new synthesis of (+)-gregatin B and the first synthesis of (−)-graminin A were achieved.