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Letter

Common-Intermediate Strategy for Synthesis of Conduritols and Inositols via β-Hydroxy Cyclohexenylsilanes

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Jung-Nyoung Heo, Edward B. Holson, and William R. Roush*

Department of Chemistry, University of Michigan, Ann Arbor, Michigan 48109

Org. Lett., 2003, 5 (10), pp 1697–1700

DOI: 10.1021/ol034349d

Publication Date (Web): April 15, 2003

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, roush@umich.edu

Abstract

Syntheses of conduritols B−D and F and d-(+)-chiro- and neo-inositols from cyclohexenylsilane intermediates are described. The key cyclohexylsilane intermediates 5 and 14 were synthesized by stereoselective olefin dihydroxylation of the corresponding cyclohexenylsilanes. Selective Peterson elimination reactions and Fleming−Tamao oxidations of 5 and 14 then delivered the targeted cyclitol derivatives.

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Published In Issue May 15, 2003
Received February 27, 2003

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Letter

Common-Intermediate Strategy for Synthesis of Conduritols and Inositols via β-Hydroxy Cyclohexenylsilanes

Abstract

Tools

SciFinder Links

History

Recommend & Share

Related Content

Enantio- and Diastereoselective Synthesis of Cyclic β-Hydroxy Allylsilanes via Sequential Aldehyde γ-Silylallylboration and Ring-Closing Metathesis Reactions

Synthesis of (+)-Bullatacin via the Highly Diastereoselective [3+2] Annulation Reaction of a Racemic Aldehyde and a Nonracemic Allylsilane

A Concise Total Synthesis of (−)-Quinocarcin via Aryne Annulation

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