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A Formal Total Synthesis of Eleutherobin Through an Unprecedented Kinetically Controlled Ring‐Closing‐Metathesis Reaction of a Densely Functionalized Diene
Author(s) -
Castoldi Damiano,
Caggiano Lorenzo,
Panigada Laura,
Sharon Ofer,
Costa Anna M.,
Gennari Cesare
Publication year - 2005
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.200461767
Subject(s) - diene , allylic rearrangement , isomerization , metathesis , ring closing metathesis , salt metathesis reaction , chemistry , total synthesis , catalysis , cleavage (geology) , stereochemistry , organic chemistry , materials science , polymerization , composite material , natural rubber , polymer , fracture (geology)
The key step in a formal total synthesis of eleutherobin was an unprecedented kinetically controlled RCM reaction of a densely functionalized diene 1 bearing two PMP‐protected allylic alcohols in the presence of a second‐generation Grubbs catalyst. Subsequent isomerization of the E 10‐membered enedione 2 to the more stable Z isomer and cleavage of the MOM protecting group led to the known precursor 3 . MOM=methoxymethyl; PMP= p ‐methoxyphenyl.