A Formal Total Synthesis of Eleutherobin Through an Unprecedented Kinetically Controlled Ring‐Closing‐Metathesis Reaction of a Densely Functionalized Diene | Zendy

Castoldi Damiano | Zendy; Caggiano Lorenzo | Zendy; Panigada Laura | Zendy; Sharon Ofer | Zendy; Costa Anna M. | Zendy; Gennari Cesare | Zendy

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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.

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