Aldolase-Catalyzed Synthesis of Conformationally Constrained Iminocyclitols: Preparation of Polyhydroxylated Benzopyrrolizidines and Cyclohexapyrrolizidines

详细信息    查看全文

• 作者：Pedro Laborda ; Francisco J. Sayago ; Carlos Cativiela ; Teodor Parella ; Jes煤s Joglar ; Pere Clap茅s
• 刊名：Organic Letters
• 出版年：2014
• 出版时间：March 7, 2014
• 年：2014
• 卷：16
• 期：5
• 页码：1422-1425
• 全文大小：270K
• 年卷期：v.16,no.5(March 7, 2014)
• ISSN：1523-7052

文摘

A straightforward chemo-enzymatic synthesis of new polyhydroxylated benzopyrrolizidines and cyclohexapyrrolizidines is developed. The two-step strategy consists of l-fuculose-1-phosphate aldolase variant F131A-catalyzed aldol addition of dihydroxyacetone phosphate to rac-N-benzyloxycarbonylindoline-2-carbaldehyde as well as (2S*,3aS*,7aS*)- and (2S*,3aR*,7aR*)-N-benzyloxycarbonyloctahydroindole-2-carbaldehydes and a subsequent one-step catalytic deprotection鈥搑eductive amination.