An Efficient Synthetic Approach to the Aromatic Sesquiterpenoids via a Smi 2 -Promoted Construction of Quaternary Centre

Abstract

The total synthesis of the natural (±)-cuparene (1) and (±)-herbertene (2) has been carried out in eight steps from 2-cyclohexen-1-one (3) via a key quaternary carbon centre construction using a SmI₂-promoted rearrangement of 2,3-epoxy alcohol.

Keywords

quaternary carbon centre 2,3-epoxy alcohol

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The NOESY spectrum for compound 9a shows the strong correlations between H-1 and Ar-H, and between H-1 and ArCH₂-H.