Jump to main content
Jump to site search

Issue 13, 2015
Previous Article Next Article

Total syntheses of five uvacalols: structural validation of uvacalol A, uvacalol B and uvacalol C and disproval of the structures of uvacalol E and uvacalol G

Author affiliations

Abstract

Uvacalols are novel carbasugars belonging to the family of C7-cyclitols, and are isolated from the roots of the medicinal plant, Uvaria calamistrata. In this study, we report the first syntheses of five uvacalols starting from a cheap and easily available chiral pool starting material, D-mannitol, in their optically pure form. D-Mannitol was converted to the alkene 2 through a series of regioselective and chemoselective transformations by following our previously reported strategies. Alkene 2 was converted to the enal 5 through a series of protective group manipulations. Enal 5 was converted to the diene 6 by the addition of vinyl magnesium bromide. Ring closing metathesis of the diene 6 using Grubbs’ second generation catalyst installed the core cyclohexenyl unit. Through several iterative and selective manipulations of various hydroxyl groups, uvacalol A, uvacalol B, uvacalol C, uvacalol E and uvacalol G were synthesized. A comparison of the 1H NMR and 13C NMR data of these synthesized molecules with the reported data, revealed that the reported structures of uvacalols A–C are correct and those of uvacalols E and G are wrong.

Graphical abstract: Total syntheses of five uvacalols: structural validation of uvacalol A, uvacalol B and uvacalol C and disproval of the structures of uvacalol E and uvacalol G

Back to tab navigation

Supplementary files

Publication details

The article was received on 24 Dec 2014, accepted on 26 Jan 2015 and first published on 26 Jan 2015


Article type: Paper
DOI: 10.1039/C4OB02663B
Author version
available:
Download author version (PDF)
Org. Biomol. Chem., 2015,13, 3900-3910

  •   Request permissions

    Total syntheses of five uvacalols: structural validation of uvacalol A, uvacalol B and uvacalol C and disproval of the structures of uvacalol E and uvacalol G

    A. Vidyasagar and K. M. Sureshan, Org. Biomol. Chem., 2015, 13, 3900
    DOI: 10.1039/C4OB02663B

Search articles by author

Spotlight

Advertisements