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A Synthetic Pathway to Either Enantiomer of Merrilactone A
Author(s) -
Meng Zhaoyang,
Danishefsky Samuel J.
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.200462509
Subject(s) - desymmetrization , enantiomer , intramolecular force , key (lock) , stereochemistry , computer science , chemistry , ring (chemistry) , enantioselective synthesis , combinatorial chemistry , information retrieval , organic chemistry , catalysis , computer security
A route to enantioenriched merrilactone A was found via intermediate 3 . A degradation pathway in which meso compound 1 is transformed into key intermediate 2 in four steps occurs with full regiocontrol and promising enantiocontrol. A key feature of this reaction sequence is the desymmetrization of 1 through an intramolecular asymmetric ring‐opening reaction.