First synthesis of (±)-1α, 2α, 4β-trihydroxycyclohex-5-ene. Anchimeric assistance in conduritol syntheses

Add time:09/06/2019    Source:sciencedirect.com

The deoxy-conduritol (1α, 2α, 4β)-1, 2, 4-trihydroxycyclohex-5-ene (6) has been prepared in racemic form from 1, 4-benzoquinone in a six-step sequence, the key reaction involving a monohalide displacement by anchimeric assistance in the diacetoxy-dibromo compound previously employed for a synthesis of conduritol-B. Evidence for the mechanism of the double halide displacement in the latter synthesis has been obtained.

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