Divergent Total Synthesis of Indoxamycins A, C, and F1. Issue 50 (31st October 2013)

• Record Type: Journal Article
• Authors: He, Chi; Zhu, Chenlong; Dai, Zhifeng; Tseng, Chih‐Chung; Ding, Hanfeng
• Is Part Of: Angewandte Chemie international edition. Volume 52:Issue 50(2013)
• Page Start: 13256
• Page End: 13260
• Publication Date: 2013-10-31
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201307426
• Languages: English
• ISSNs: 1433-7851

Abstract

<abstract abstract-type="graphical" xml:lang="en"> <title> <x xml:space="preserve">Abstract</x> </title> <p> <bold>The concise and divergent</bold> total synthesis of (−)‐indoxamycins A, C, and F has been completed for the first time by using a tricyclic enone as the common late‐stage intermediate. The key steps of the strategy are based on an Ireland–Claisen rearrangement, a stereodivergent reductive 1, 6‐enyne cyclization, and a tandem 1, 2‐addition/oxa‐Michael/methylenation reaction.<boxed-text content-type="graphic" position="anchor" orientation="portrait"><graphic position="anchor" mimetype="image" xlink:href="ark:/27927/pgg4t3kjrnx" orientation="portrait" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink" /></boxed-text></p> </abstract>