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An Enantiospecific Synthesis of Jiadifenolide
Author(s) -
Siler David A.,
Mighion Jeffrey D.,
Sorensen Erik J.
Publication year - 2014
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201402335
Subject(s) - natural product , chemistry , annulation , propellane , stereochemistry , reagent , pulegone , synthon , combinatorial chemistry , organic chemistry , bicyclic molecule , catalysis , chromatography , essential oil
A Robinson annulation, van Leusen homologation, and a desymmetrizing CH oxidation enabled an enantiospecific synthesis of the neurotrophic natural product jiadifenolide. From a pulegone‐derived building block, a key propellane intermediate was constructed through the use of simple reagents in a highly diastereoselective fashion. A short series of oxidations of this tricylic framework allowed progression to the natural product.