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

✍ Scribed by Alan H. Haines; Amy S.H. King; Jonathan R. Knight; Viet-Anh Nguyen

Book ID
104259318
Publisher
Elsevier Science
Year
1998
Tongue
French
Weight
239 KB
Volume
39
Category
Article
ISSN
0040-4039

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✦ Synopsis

The deoxy-conduritol (lct,2ot,4l~)-l,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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