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Total Synthesis of Aspergillide A and B Based on the Transannular Oxy‐Michael Reaction
Author(s) -
Kanematsu Makoto,
Yoshida Masahiro,
Shishido Kozo
Publication year - 2011
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.201007327
Subject(s) - michael reaction , tetrahydropyran , metathesis , total synthesis , chemistry , salt metathesis reaction , stereochemistry , organic chemistry , ring (chemistry) , catalysis , polymer , polymerization
Keys to the kingdom : A highly efficient and diastereoselective transannular oxy‐Michael reaction for the construction of the syn ‐ and anti ‐tetrahydropyran units from a common 14‐membered macrolactone is the key step for the total synthesis of aspergillide A and B (see scheme; CM=cross‐metathesis, HWE=Horner–Wadsworth–Emmons, TBS= tert ‐butyldimethylsilyl).