Enantioselective Synthesis of Protected Nitrocyclohexitols with Five Stereocenters. Total Synthesis of (+)-Pancratistatin

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• 作者：Fernando Cagide-Fag铆n ; Olaia Nieto-Garc铆a ; Hugo Lago-Santom茅 ; Ricardo Alonso
• 刊名：The Journal of Organic Chemistry
• 出版年：2012
• 出版时间：December 21, 2012
• 年：2012
• 卷：77
• 期：24
• 页码：11377-11382
• 全文大小：306K
• 年卷期：v.77,no.24(December 21, 2012)
• ISSN：1520-6904

文摘

2-Methoxymethylpyrrolidine best performed, among several other proline derivatives, to control the enantioselective [3+3] annulation of 尾-(hetero)aryl-伪-nitro-伪,尾-enals with commercial 2,2-dimethyl-1,3-dioxan-5-one, a procedure that renders highly oxygenated nitrocyclohexanes endowed with five new stereocenters. Use of this reaction allowed the development of a total synthesis of the antitumoral natural product (+)-pancratistatin; it also converted our previous racemic route to tetrodotoxin into an enantioselective one.