Efficient Syntheses of Traumatic Lactone and Rhizobialide
Jing Zhou1, Shihua Song1, Feng Jiang1
1Department Laboratory of Molecular Recognition and Synthesis, Department of Chemistry, Zhejiang University, 310027, Hangzhou city, Zhejiang, P. R. China.
Abstract:
Herein, we report the total synthesis of traumatic lactone and rhizobialide by utilizing allenoic acid to construct the lactone ring. The key starting materials, allenoic acids, could be prepared by the ATA (allenation of terminal alkynes) of a terminal alkyne with an aldehyde that contained a protected hydroxyl group followed by hydrolysis. Importantly, the asymmetric synthesis could be realized just by replacing racemic diphenylprinol with (R)- or (S)-diphenylprinol to deliver the optically active allenoate.
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