De Novo Synthesis of the Trisaccharide Subunit of Landomycins A and E
详细信息 查看全文
- 作者：Maoquan Zhou ; George A. O’ ; Doherty
- 刊名：Organic Letters
- 出版年：2008
- 出版时间：June 5, 2008
- 年：2008
- 卷：10
- 期：11
- 页码：2283 - 2286
- 全文大小：382K
- 年卷期：v.10,no.11(June 5, 2008)
- ISSN：1523-7052
文摘
A highly enantio- and diastereoselective synthesis of α-L-rhodinose, β-D-olivose as well as the trisaccharide portion of landomycin A from achiral acetyl furan has been developed. The key transformations include the palladium-catalyzed glycosylation, Myers’ reductive rearrangement, diastereoselective dihydroxylation, and regioselective Mitsunobu inversion. A Mitsunobu reaction on a six member ring cis-1,2-diol was found to chemoselectively discriminate between equatorial and axial alcohols and to stereoselectively convert cis-1,2-diol into anti-1,2-diol.