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
Full Text: HTML
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 ...
Related Articles:
The structures of huperzine A and B, two new alkaloids exhibiting marked anticholinesterase activity
[Tudhope, Stephen R.; Bellamy, Julie A.; Ball, Anthony; Rajasekar, Dewakar; Azadi-Ardakani, Manouchehr; Meera, Harihara Subramanian; Gnanadeepam, Jesudoss Mercy; Saiganesh, Ramanathan; Gibson, Frank; He, Linli; Behrens, Carl H.; Underiner, Gail; Marfurt, Judith; Favre, Nathalie Organic Process Research and Development, 2012 , vol. 16, # 4 p. 635 - 642]
Synthesis of huperzine A, its analogs, and their anticholinesterase activity
[Kozikowski; Xia; Reddy; Tuckmantel; Hanin; Tang Journal of Organic Chemistry, 1991 , vol. 56, # 15 p. 4636 - 4645]
Synthesis of huperzine A, its analogs, and their anticholinesterase activity
[Kozikowski; Xia; Reddy; Tuckmantel; Hanin; Tang Journal of Organic Chemistry, 1991 , vol. 56, # 15 p. 4636 - 4645]