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Synthesis 2008(19): 3142-3147  
DOI: 10.1055/s-2008-1067260
SPECIALTOPIC
© Georg Thieme Verlag Stuttgart ˙ New York

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

Giovanni Luchettia, Kejia Dingb, 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;
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Publication History

Received 20 May 2008
Publication Date:
05 September 2008 (online)

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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

16

After our original disclosure of these results (ref. 14), Madsen and co-workers reported that performing this reaction with vinylmagnesium chloride in toluene leads to a higher (5:1) syn selectivity (ref. 15b).

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Both the organometallic reagent and the reaction solvent are important since Lewis basic solvents such as THF or Et2O can diminish chelation by strongly coordinating to the metal species.