Enantioselective Organocatalytic Construction of Hexahydropyrroloindole by Means of α‐Alkylation of Aldehydes Leading to the Total Synthesis of (+)‐Gliocladin C. Issue 10 (10th February 2013)

• Record Type: Journal Article
• Authors: Song, Jin; Guo, Chang; Adele, Arafate; Yin, Hao; Gong, Liu‐Zhu
• Is Part Of: Chemistry. Volume 19:Issue 10(2013)
• Page Start: 3319
• Page End: 3323
• Publication Date: 2013-02-10
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201204522
• Languages: English
• ISSNs: 0947-6539

Abstract

<abstract abstract-type="graphical" xml:lang="en"> <title> <x xml:space="preserve">Abstract</x> </title> <p> <bold>12‐Step program</bold>: The combined use of cinchona alkaloid based amine and chiral phosphoric acid enabled the asymmetric alkylation reaction of 3‐hydroxyoxindoles with aldehydes to give 3, 3′‐disubstituted oxindoles in excellent enantioselectivities, which allows for the enantioselective total synthesis of (+)‐gliocladin C in 12 steps from 3‐hydroxyoxindole with 19 % overall yield (see scheme; PMB=<italic>para</italic>‐methoxybenzyl).<boxed-text content-type="graphic" position="anchor" orientation="portrait"><graphic position="anchor" mimetype="image" xlink:href="ark:/27927/pgg1v4fk9gw" orientation="portrait" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink" /></boxed-text></p> </abstract>