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Synthesis 2008(19): 3155-3159  
DOI: 10.1055/s-2008-1067261
SPECIALTOPIC
© Georg Thieme Verlag Stuttgart ˙ New York

Facile Enantiospecific Synthesis of Dihydroconduritols E and F

Kavirayani R. Prasad*, Amit B. Pawar
Department of Organic Chemistry, Indian Institute of Science, Bangalore 560012, India
Fax: +91(80)23600529; e-Mail: prasad@orgchem.iisc.ernet.in;
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Publication History

Received 15 May 2008
Publication Date:
05 September 2008 (online)

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Abstract

An enantiospecific synthesis of cyclohexane-1,2,3,4-tetrols was accomplished from l-(+)-tartaric acid. Pivotal steps in the synthetic sequence include zinc-mediated Boord-type fragmentation of an acetonide, ring-closing metathesis (RCM), and osmium-mediated dihydroxylation.

Key words

cyclitols - ring-closing metathesis - tartaric acid - Boord fragmentation

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Stereochemistry of 18 was further proved by X-ray crystal structure analysis. (The crystallographic data has been deposited with The Cambridge Crystallographic Data Centre, CCDC687686). This data can be obtained free of charge from The Cambridge Crystallographic Data Centre via http://www.ccdc.cam.ac.uk/data request/cif.