Issue 41, 2013
From the journal:

RSC Advances

Stereoselectivity of A-ring contraction for 3-oxotriterpenoids†

Alexey D. Kacharov,a   Sergiy V. Yemets,a   Victor N. Nemykin,b   Liliya M. Kacharova,a   Andrey A. Fokinc  and  Pavel A. Krasutsky*a  

* Corresponding authors

a Natural Resources Research Institute, University of Minnesota, 5013 Miller Trunk Highway, Duluth, MN 55811, United States
E-mail: pkrasuts@nrri.umn.edu

b Department of Chemistry and Biochemistry, University of Minnesota Duluth, 1039 University Drive, Duluth, MN 55812, United States

c Department of Organic Chemistry, Kiev Polytechnic Institute, pr. Pobedy 37, 03056 Kiev, Ukraine

Abstract

The A-ring oxidation/contraction of 3-oxotriterpenoids was developed as a two-step and “one pot” process. A benzylic acid type rearrangement of triterpenoid diosphenols gives (S)- as major and (R)-α-hydroxycarboxylic acids as minor reaction products. The absolute configurations were determined from the X-ray crystal structure analysis. The mechanism of ring contraction was modelled computationally at the DFT and MP2 levels of theory. The tautomeric triterpenoid A-seco δ-oxocarboxylic acids and A-ring hydroxy lactones formed after deep oxidation/acidification of 3-oxotriterpenoids.

Graphical abstract: Stereoselectivity of A-ring contraction for 3-oxotriterpenoids

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Article information

DOI
https://doi.org/10.1039/C3RA42929F
Article type
Paper
Submitted
24 Jun 2013
Accepted
29 Jul 2013
First published
30 Jul 2013

RSC Adv., 2013,3, 19057-19063

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Stereoselectivity of A-ring contraction for 3-oxotriterpenoids

A. D. Kacharov, S. V. Yemets, V. N. Nemykin, L. M. Kacharova, A. A. Fokin and P. A. Krasutsky, RSC Adv., 2013, 3, 19057 DOI: 10.1039/C3RA42929F

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