Enantio- and Diastereodivergent
Synthetic Route to Multifarious Cyclitols from d-Xylose
via Ring-Closing Metathesis

Giovanni Luchetti; Kejia Ding; Marc d’Alarcao; Alexander Kornienko

doi:10.1055/s-2008-1067260

SPECIALTOPIC

Enantio- and Diastereodivergent Synthetic Route to Multifarious Cyclitols from d-Xylose via Ring-Closing Metathesis

Giovanni Luchetti^a, Kejia Ding^b, Marc d’Alarcao*^b, Alexander Kornienko*^a
^a Department of Chemistry, New Mexico Institute of Mining and Technology, Socorro, NM 87801, USA
Fax: +1(575)8355364; e-Mail: akornien@nmt.edu;
^b Department of Chemistry, San José State University, One Washington Square, San José, CA 95192-0101, USA
Fax: +1(408)9244945; e-Mail: mdalarcao@science.sjsu.edu;

Abstract

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Abstract

Short stereoselective syntheses of various cyclitols, including the derivatives of conduritol B, conduritol F, myo-inositol, and chiro-inositol have been accomplished. The key steps in the syntheses are a ring-closing metathesis process and a diastereodivergent organometallic addition to a d-xylose-derived aldehyde.

Key words

conduritol - inositol - Grignard - stereochemistry model - chelation - Felkin-Anh - cyclophellitol - latent symmetry

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References

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