Total Synthesis and Structural Reassignment of Lyngbyaloside C Highlighted by Intermolecular Ketene Esterification. Issue 30 (23rd June 2015)

• Record Type: Journal Article
• Authors: Chang, Chia‐Fu; Stefan, Eric; Taylor, Richard E.
• Is Part Of: Chemistry. Volume 21:Issue 30(2015)
• Page Start: 10681
• Page End: 10686
• Publication Date: 2015-06-23
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201502132
• Languages: English
• ISSNs: 0947-6539

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>Lyngbyaloside C, a classic macrolide, isolated from Lyngbya bouilloni, has shown moderate anticancer activity against several cancer cell lines. Here, we report the first total synthesis and stereochemical configuration reassignment of lyngbyaloside C. The synthesis highlights a one‐pot intermolecular ketene esterification reaction to form the crucial tertiary ester and tetrahydropyran. In addition, a novel and concise synthetic pathway towards the 1, 3‐<italic>syn</italic> secondary, tertiary diol fragment is described using a regio‐ and stereospecific electrophilic ether transfer reaction.</p> </abstract>