Semisynthesis and DFT Study of New Michael Adducts using (E)-α-Atlantone, Isolated from Cedrus atlantica Essential Oil

Rida Nejjari; Maryam Bashir; Houria Raji; Bouchra Es-Sounni; Mohamed Adardour; Farhan Siddique; Mohamed Bakhouch; Abdelkrim Mouzdahir; Ahmed Benharref; Noureddine Mazoir; Samir Chtita

doi:10.2174/0115701786321643240709114001

ISSN: 1570-1786
E-ISSN: 1875-6255

Semisynthesis and DFT Study of New Michael Adducts using (E)-α-Atlantone, Isolated from Cedrus atlantica Essential Oil
Authors: Rida Nejjari¹, Maryam Bashir², Houria Raji³, Bouchra Es-Sounni¹, Mohamed Adardour⁴, Farhan Siddique², Mohamed Bakhouch¹, Abdelkrim Mouzdahir¹, Ahmed Benharref³, Noureddine Mazoir¹ and Samir Chtita⁵
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¹ Bioorganic Chemistry Team, Faculty of Science, Chouaïb Doukkali University, P.O. Box 24, 24000 El Jadida, Morocco ; ² Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Bahauddin Zakariya University 60800, Multan, Pakistan ; ³ Laboratory of Natural Substances Chemistry, Faculty of Sciences Semlalia, Cadi Ayyad University, P.O. Box 2390, 40000, Marrakech, Morocco ; ⁴ Laboratory of Molecular Chemistry, Faculty of Sciences Semlalia, Cadi Ayyad University, P.O. Box 2390, 40000, Marrakech, Morocco ; ⁵ Laboratory of Analytical and Molecular Chemistry, Faculty of Sciences Ben M’Sik, Hassan II University of Casablanca, P.O. Box 7955 Casablanca, Morocco
Source: Letters in Organic Chemistry, Volume 22, Issue 3, Mar 2025, p. 228 - 241
DOI: https://doi.org/10.2174/0115701786321643240709114001
- Received: 06 Apr 2024
- Accepted: 10 Jun 2024
- Available online: 15 Jul 2024

Abstract

This work is devoted to the synthesis of divers Michael adducts from (E)-α-atlantone as an α,β-unsaturated ketone isolated from Cedrus atlantica essential oil. The (E)-α-atlantone is subjected to ethyl cyanoacetate, phenylmagnesium bromide, and ethanol to produce the corresponding 1,4-Michael adducts in good yields. The conjugate addition of the appropriate reagents onto (E)-α-atlantone proceeds in a regiospecific manner, closely governed by the nucleophilicity of the reagents as well as their stereospecific blocking. The structure of the obtained Michael adducts is established using NMR (¹H & ¹³C) spectroscopy and elemental analysis. Likewise, the DFT method was utilized to comprehend the molecular properties, stability, and reactivity of the investigated compounds, as well as to explain the proposed mechanism. The computed outcomes are in good agreement with the experimental data.

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Semisynthesis and DFT Study of New Michael Adducts using (E)-α-Atlantone, Isolated from Cedrus atlantica Essential Oil

Letters in Organic Chemistry 22, 228 (2025); https://doi.org/10.2174/0115701786321643240709114001

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Article Type: Research Article

Keyword(s): (E)-α-atlantone; Cedrus atlantica; DFT; mechanistic study; Michael adducts; Semisynthesis

Semisynthesis and DFT Study of New Michael Adducts using (E)-α-Atlantone, Isolated from Cedrus atlantica Essential Oil

Abstract

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Supplementary material is available on the publisher’s website along with the published article.

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