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A Sequential Two‐Component Etherification/Oxa‐Conjugate Addition Reaction: Asymmetric Synthesis of (+)‐Leucascandrolide A Macrolactone
Author(s) -
Evans P. Andrew,
Andrews William J.
Publication year - 2008
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.200801357
Subject(s) - tetrahydropyran , yield (engineering) , conjugate , sequence (biology) , stereochemistry , chemistry , component (thermodynamics) , combinatorial chemistry , mathematics , ring (chemistry) , organic chemistry , materials science , physics , biochemistry , mathematical analysis , metallurgy , thermodynamics
A smooth operator : The asymmetric synthesis of the macrolactone of (+)‐leucascandrolide A (see structure) has been accomplished through a convergent route (longest linear sequence of 14 steps) in 20 % overall yield. The assembly of the 1,5‐bis(tetrahydropyran) core in a single operation provides the most concise synthetic approach developed to date.