Issue 14, 1994

(–)-Quinic acid in organic synthesis. Part 4. Syntheses of cyclophellitol and its (1R, 6S)-, (2S)-, (1R, 2S, 6S)-diastereoisomers

Abstract

Cyclophellitol 1 and its (1R, 6S)-, (2S)-, (1R, 2S, 6S)-diastereoisomers 2, 3 and 4 are constructed from quinic acid involving the following key steps: regioselective cyclic sulfate ring opening, regiospecific oxidative elimination and an epoxidation. Diastereoisomers 1, 2, 3 and 4 are characterized as their corresponding tetraacetates 5, 6, 7 and 8.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1994, 2017-2025

(–)-Quinic acid in organic synthesis. Part 4. Syntheses of cyclophellitol and its (1R, 6S)-, (2S)-, (1R, 2S, 6S)-diastereoisomers

T. K. M. Shing and V. W.-F. Tai, J. Chem. Soc., Perkin Trans. 1, 1994, 2017 DOI: 10.1039/P19940002017

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