Collective Synthesis of 4‐Hydroxy‐2‐pyridone Alkaloids and Their Antiproliferation Activities. Issue 9 (22nd July 2014)

• Record Type: Journal Article
• Authors: Ding, Feiqing; Leow, Min Li; Ma, Jimei; William, Ronny; Liao, Hongze; Liu, Xue‐Wei
• Is Part Of: Chemistry, an Asian journal. Volume 9:Issue 9(2014:Sep.)
• Page Start: 2548
• Page End: 2554
• Publication Date: 2014-07-22
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1002/asia.201402466
• Languages: English
• ISSNs: 1861-4728

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>A collective synthesis of 4‐hydroxy‐2‐pyridone alkaloids—specifically, pretenellin B, prebassianin B, farinosone A, militarione D, pyridovericin, and torrubiellone C—has been achieved. Key steps include using a strategic convergent method to synthesize the densely substituted pyridone key <named-content content-type="reactionType" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink">intermediate</named-content> by <named-content content-type="reactionType" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink">Suzuki–Miyaura</named-content><named-content content-type="reactionType" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink">cross‐coupling reaction</named-content>, a divergent synthesis approach of target molecules by <named-content content-type="reactionType" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink">aldol condensation</named-content> of pyridone <named-content content-type="reactionType" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink">intermediate</named-content> with homologous aldehydes, and an iterative synthesis of homologous aldehydes with all‐<italic>trans</italic>‐polyene backbones. Interestingly, among the six tumor cell lines investigated, torrubiellone C was found to induce potent and apoptotic inhibitory activities on Jurkat T cells with IC<sub>50</sub> values of 7.05 μ<sc>M</sc>. Hence, this approach could potentially contribute to the synthesis of bioactive small‐molecule libraries as well as drug discovery.</p> </abstract>