Total Synthesis and Stereochemical Reassignment of Mandelalide A1. Issue 25 (18th May 2014)

• Record Type: Journal Article
• Authors: Lei, Honghui; Yan, Jialei; Yu, Jie; Liu, Yuqing; Wang, Zhuo; Xu, Zhengshuang; Ye, Tao
• Is Part Of: Angewandte Chemie international edition. Volume 53:Issue 25(2014)
• Page Start: 6533
• Page End: 6537
• Publication Date: 2014-05-18
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201403542
• Languages: English
• ISSNs: 1433-7851

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>The total synthesis of the tunicate metabolite mandelalide A and the correction of its originally assigned stereochemistry are reported. Key features of the convergent, fully stereocontrolled route include the use of a Prins cyclization for the diastereoselective construction of the tetrahydropyran subunit, Rychnovsky–Bartlett cyclization for the preparation of the tetrahydrofuran moiety, Suzuki coupling, Horner–Wadsworth–Emmons macrocyclization, and glycosylation to append the <sc>L</sc>‐rhamnose‐derived pyranoside.</p> </abstract>