A One-Pot Preparation of Aryl- and Heteroarylcycloalkenes: Application to the Total Synthesis of (±)-Laurokamurene B

Abstract

A general one-pot method has been developed for the preparation of various aryl- and heteroarylcycloalkenes. After lithiation of aryl and heteroaryl bromides followed by transmetalation with CeCl₃, the organocerium addition to cycloalkanones proceeds cleanly to provide the intermediate alkoxide. Addition of MsCl or SOCl₂ with DBU gave aryl-substituted cycloalkenes in good yields. A short total synthesis of (±)-laurokamurene B making use of this reaction is described.

Key words

organocerium reagents - addition reactions - eliminations - arylcycloalkenes - laurokamurene B

References and Notes

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18

Srikrishna et al.^¹6c did not succeed to purify the ketone 5 and characterized this one as the corresponding tosylhydrazone.