Journal of Organic Chemistry
Journal of Organic Chemistry
4 years ago

Diastereoselective Intramolecular Heck Reaction Assisted by an Acetate Group: Synthesis of the Decahydrobenzofluorene Derivative Dasyscyphin E

Diastereoselective Intramolecular Heck Reaction Assisted by an Acetate Group: Synthesis of the Decahydrobenzofluorene Derivative Dasyscyphin E
Ettahir Boulifa, Enrique Alvarez-Manzaneda, Rachid Chahboun, Ramón Alvarez-Manzaneda, Fermín Jiménez, Ahmed Ibn Mansour, Antonio Fernández
The first synthesis of antifungal sesquiterpene quinol dasyscyphin E was achieved starting from trans-communic acid. The process described involves the first diastereoselective synthesis of this type of compound by cyclization of an aryl bicyclosesquiterpene. The acid was efficiently transformed into a sesquiterpene synthon, which was converted into the corresponding bromoaryl sesquiterpene. The key step of synthetic sequence was the cyclization of the latter under Heck reaction conditions, which yielded the tetracyclic skeleton of the target compound with complete diastereoselectivity. The participation of an acetate group is decisive, both for the course of the Heck reaction and for the stereoselectivity of the process.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b01551

DOI: 10.1021/acs.joc.7b01551

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