Synthesis of fluorinated drimanes. Preparation of 9αF-drimenin |
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Authors: | Antonio Abad Consuelo AgullóAna C Cuñat David Pardo |
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Institution: | Departamento de Qu?́mica Orgánica, Universitat de Valencia, Dr. Moliner 50, 46100 Burjassot (Valencia), Spain |
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Abstract: | A stereoselective approach to the 9α-fluorinated analogue of the natural drimane sesquiterpene drimenin starting from β-ionone is described. β-Ionone is transformed into a bicyclic β-cetoester from which 9αF-drimenin is prepared through stereoselective electrophilic fluorination at the C-9 with N-fluorobenzenesulfonimide followed by Wittig methylenation, allylic bromination, bromine-hydroxyl exchange and γ-lactonization. |
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