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Three Rings in One Step: A Quick Approach to IKD‐8344
Author(s) -
Zou Yang,
Wu Yikang
Publication year - 2012
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201201395
Subject(s) - racemization , intramolecular force , computer science , enantioselective synthesis , scheme (mathematics) , information retrieval , competition (biology) , stereochemistry , chemistry , mathematics , organic chemistry , biology , mathematical analysis , catalysis , ecology
A highly efficient enantioselective total synthesis of the natural antibiotic IKD‐8344 is achieved through a convergent route. This route features an otherwise impossible concurrent formation of the THF rings from a linear polyketide precursor through intramolecular O alkylations of mesylates in competition with normally rather facile β elimination and/or α racemization reactions (see scheme, Ms=methanesulfonyl).