Asymmetric Synthesis of Spiroketal, Spiroether, and Oxabicycle Building Blocks via Stereoselective Spiro- and Bicycloannulation of 2-Hydroxy Dihydropyrans
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- 作者：Michal Lejkowski ; Prabal Banerjee ; Jan Runsink ; Hans-Joachim Gais
- 刊名：Organic Letters
- 出版年：2008
- 出版时间：July 3, 2008
- 年：2008
- 卷：10
- 期：13
- 页码：2713 - 2716
- 全文大小：162K
- 年卷期：v.10,no.13(July 3, 2008)
- ISSN：1523-7052
文摘
A modular asymmetric synthesis of spiroketal, spiroether, and oxabicycle building blocks is described based on the spiro- and bicycloannulation of α-hydroxy dihydropyrans, which were obtained from sulfoximine-substituted homoallylic alcohols. Key steps of the syntheses are stereoselective Ferrier-type O- and C-glycosidation, ring-closing metathesis, and stereoselective Prins cyclization.