Chemistry Letters, Vol.42, No.10, 1273-1275, 2013
Synthesis of Methyl epi-Anhydroquinate Utilizing [2,3]-Sigmatropic Rearrangement of Iodosoalkene
Sigmatropic rearrangement has been utilized for stereoselective syntheses of structurally complicated natural products because of its high stereoselectivity and reactivity. Quinic acid (1) and its epimer 2 are versatile building blocks for the preparation of various bioactive compounds. We report the synthesis of methyl epi-anhydroquinate 3 via the [2,3]-sigmatropic rearrangement of iodosoalkene.