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Total Synthesis and Stereochemical Reassignment of Mandelalide A
Author(s) -
Lei Honghui,
Yan Jialei,
Yu Jie,
Liu Yuqing,
Wang Zhuo,
Xu Zhengshuang,
Ye Tao
Publication year - 2014
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201403542
Subject(s) - tetrahydropyran , chemistry , total synthesis , stereochemistry , moiety , prins reaction , tetrahydrofuran , tunicate , glycosylation , organic chemistry , ring (chemistry) , solvent , biochemistry , ecology , biology , catalysis
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 L ‐rhamnose‐derived pyranoside.