Tetrahedron

Target-oriented multifunctional organocatalysis for enantioselective synthesis of bicyclo [3.3. 1] nona-2, 6-dien-9-ones. A formal asymmetric synthesis of huperzine A

XH Ding, X Li, D Liu, WC Cui, X Ju, S Wang, ZJ Yao

Index: Ding, Xiao-Hua; Li, Xiang; Liu, Dan; Cui, Wei-Chen; Ju, Xuan; Wang, Shaozhong; Yao, Zhu-Jun Tetrahedron, 2012 , vol. 68, # 31 p. 6240 - 6248

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Citation Number: 11

Abstract

A target-oriented highly enantioselective multifunctional organocatalytic approach has been developed to construct the bicycle-[3.3. 1] nona-2, 6-dien-9-one core of (−)-huperzine A for the first time, with up to 95% ee in the gram-scale procedure. The newly established methodology is also eligible to synthesize a variety of bicyclo [3.3. 1] nona-2, 6-dien-9-ones in high enantiopurities, and thus is useful for the future development of novel huperzine A ...