Locked Nucleosides Based on Oxabicyclo[3.2.1]octane and Oxabicyclo[2.2.1]heptane Skeletons
详细信息 查看全文
- 作者：Ramprasad Ghosh ; Joy Krishna Maity ; Basudeb Achari ; Sukhendu B Mandal
- 刊名：Journal of Organic Chemistry
- 出版年：2010
- 出版时间：April 2, 2010
- 年：2010
- 卷：75
- 期：7
- 页码：2419-2422
- 全文大小：845K
- 年卷期：v.75,no.7(April 2, 2010)
- ISSN：1520-6904
文摘
Intramolecular nitrone cycloaddition (INC) reaction on a d-glucose derived substrate carrying an allyl group at C-1 and an enose-nitrone at C-5 or an aldehyde-nitrone at C-1 and vinyl group at C-4 furnished a tricyclo[6.2.1.02,6]undecane or a tricyclo[5.2.1.02,6]decane ring structure. These tricycles were converted to bicylic nucleosides with oxabicyclo[3.2.1]octane and oxabicyclo[2.2.1]heptane rings in three steps. An oxabicyclo[3.2.1]octane ring compound could alternatively be formed by RCM reaction between C-1−allyl and C-4−vinyl moieties and transformed to nucleoside analogues through a nucleophilic substitution reaction. Participation of a neighboring benzyl ether substituent in one case paved the way for an enantiodivergent synthesis.