Practical synthesis of all inositol stereoisomers from myo-inositol

Sung Kee Chung; Yong Uk Kwon

doi:10.1016/S0960-894X(99)00348-0

Practical synthesis of all inositol stereoisomers from myo-inositol

Sung Kee Chung, Yong Uk Kwon

Department of Chemistry & Nanoscience

Research output: Contribution to journal › Article › peer-review

27 Scopus citations

Abstract

Synthesis of six inositol stereoisomers was successfully carried out via conduritol intermediates prepared from myo-inositol. Dihydroxylation and epoxidation followed by ring opening of the conduritol B, C and F derivatives gave epi-, allo-, muco-, neo-, DL-chiro- and scyllo-inositol. The cis- inositol derivative, which may not be prepared by this approach, was synthesized in 5 steps via 2-O-benzoyl-myo-inositol orthoformate as the key intermediate.

Original language	English
Pages (from-to)	2135-2140
Number of pages	6
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	9
Issue number	15
DOIs	https://doi.org/10.1016/S0960-894X(99)00348-0
State	Published - 2 Aug 1999

Bibliographical note

Funding Information:
Acknowledgment. This work was supported by the Korea Science & Engineering Foundation/Center for

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title = "Practical synthesis of all inositol stereoisomers from myo-inositol",

abstract = "Synthesis of six inositol stereoisomers was successfully carried out via conduritol intermediates prepared from myo-inositol. Dihydroxylation and epoxidation followed by ring opening of the conduritol B, C and F derivatives gave epi-, allo-, muco-, neo-, DL-chiro- and scyllo-inositol. The cis- inositol derivative, which may not be prepared by this approach, was synthesized in 5 steps via 2-O-benzoyl-myo-inositol orthoformate as the key intermediate.",

author = "Chung, {Sung Kee} and Kwon, {Yong Uk}",

note = "Funding Information: Acknowledgment. This work was supported by the Korea Science & Engineering Foundation/Center for",

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AB - Synthesis of six inositol stereoisomers was successfully carried out via conduritol intermediates prepared from myo-inositol. Dihydroxylation and epoxidation followed by ring opening of the conduritol B, C and F derivatives gave epi-, allo-, muco-, neo-, DL-chiro- and scyllo-inositol. The cis- inositol derivative, which may not be prepared by this approach, was synthesized in 5 steps via 2-O-benzoyl-myo-inositol orthoformate as the key intermediate.

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Practical synthesis of all inositol stereoisomers from myo-inositol

Abstract

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