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Synthesis of ent ‐Nanolobatolide
Author(s) -
Cheng Hau Man,
Tian Weiwei,
Peixoto Philippe A.,
Dhudshia Bhartesh,
Chen David Y.K.
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.201100926
Subject(s) - intramolecular force , enantiomer , chemistry , ring (chemistry) , menthone , stereochemistry , total synthesis , epoxide , computer science , combinatorial chemistry , organic chemistry , menthol , catalysis
Efficient and adaptable : The key steps in the total synthesis of ent ‐nanolobatolide, the enantiomer of the novel and potent neuroprotective agent, involve an oxidative ring expansion of (−)‐menthone, a Nazarov cyclization, an intermolecular Diels–Alder reaction, and an intramolecular epoxide‐opening reaction (see scheme). The two latter transformations provided evidence in support of the speculated biosynthetic pathway.