Stereoselectivity of A-ring contraction for 3-oxotriterpenoids

Alexey D. Kacharov, Sergiy V Yemets, Victor N. Nemykin, Liliya M. Kacharova, Andrey A. Fokin, Pavel A. Krasutsky

Research output: Contribution to journalArticlepeer-review

3 Scopus citations

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.

Original languageEnglish (US)
Pages (from-to)19057-19063
Number of pages7
JournalRSC Advances
Volume3
Issue number41
DOIs
StatePublished - Nov 7 2013

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