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Total Synthesis and Structural Reassignment of Lyngbyaloside C Highlighted by Intermolecular Ketene Esterification
Author(s) -
Chang ChiaFu,
Stefan Eric,
Taylor Richard E.
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201502132
Subject(s) - ketene , tetrahydropyran , chemistry , electrophile , intramolecular force , stereochemistry , intermolecular force , ether , stereospecificity , diol , total synthesis , molecule , organic chemistry , ring (chemistry) , catalysis
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‐ syn secondary, tertiary diol fragment is described using a regio‐ and stereospecific electrophilic ether transfer reaction.