Synthesis of Furanose Spirooxindoles via 1, 8‐Diazabicyclo[5.4.0]undec‐7‐ene (DBU)‐Catalyzed Aldol Reactions of a Pyruvic Aldehyde Derivative. Issue 4 (18th March 2014)

• Record Type: Journal Article
• Authors: Zhang, Dongxin; Johnson, Sherida; Cui, Hai‐Lei; Tanaka, Fujie
• Is Part Of: Asian journal of organic chemistry. Volume 3:Issue 4(2014:Apr.)
• Page Start: 391
• Page End: 394
• Publication Date: 2014-03-18
• Subjects: Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; 547.005
• DOI: 10.1002/ajoc.201400016
• Languages: English
• ISSNs: 2193-5807

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>Spirooxindoles are important compounds as they are often found in bioactive molecules. Thus, the development of new spirooxindoles and of synthetic routes to spirooxindoles is a great interest to discover new biofunctional molecules and therapeutic leads. We developed a concise method for the synthesis of spirooxindoles bearing a furanose unit. 1, 8‐Diazabicyclo[5.4.0]undec‐7‐ene (DBU) was used for an aldol reaction of a pyruvic aldehyde derivative with isatin; reduction of the ketone group was followed by treatment with acid to generate the spirofuranose unit. A set of furanose spirooxindoles were obtained in good to high yields.</p> </abstract>