Stereoselective Total Synthesis and Structural Elucidation of (−)‐Indoxamycins A–F. Issue 46 (26th September 2014)

• Record Type: Journal Article
• Authors: He, Chi; Zhu, Chenlong; Wang, Bingnan; Ding, Hanfeng
• Is Part Of: Chemistry. Volume 20:Issue 46(2014)
• Page Start: 15053
• Page End: 15060
• Publication Date: 2014-09-26
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201403986
• Languages: English
• ISSNs: 0947-6539

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>In this study, a concise and stereoselective approach for the divergent total synthesis of (−)‐indoxamycins A–F is described. The key steps of the strategy include an Ireland–Claisen rearrangement, an enantioselective 1, 6‐enyne reductive cyclization, and a tandem 1, 2‐addition/oxa‐Michael/methylenation reaction. The relative and absolute configuration of these natural products has been unambiguously elucidated, and their cytotoxic activities against HT‐29 and A‐549 tumor cell lines are also reported.</p> </abstract>