Ferrier Carbocyclization Reaction

The Ferrier carbocyclization reaction is an important carbohydrate-based transformation in organic synthesis. The reaction is highly effective for the conversion of readily available aldohexoses into enantiomerically pure cyclohexanones. This chapter focuses on the Ferrier carbocyclization reaction and its applications to natural product synthesis. Chiral cyclohexanones obtained by the Ferrier carbocyclization reaction are useful precursors for the synthesis of cyclitols and aminocyclitols, some of which are found in clinically important aminoglycoside antibiotics. The substrates for the Ferrier carbocyclization reaction are 6-deoxy-hex-5-enopyrano side derivatives. The chapter provides an overview of some representative syntheses of 5-enopyranosides. The applications of Ferrier carbocyclization reaction include the syntheses of hygromycin A, lycoricidine, (-)- and (+)-actinoboline, galanthamine, rapamycin, and morphine.