Iodine-Mediated Aromatization of Himachalenes: Synthesis of Dehydro-7,8-arylhimachalene

IF 0.7 4区化学 Q4 CHEMISTRY, ORGANIC

Letters in Organic Chemistry Pub Date : 2024-04-17 DOI:10.2174/0115701786297846240408070836

Louchachha Isam, Edder Youssef, Faris Abdelmajid, Brahim Boualy, Mustapha Ait Ali, Abdallah Karim

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引用次数: 0

Abstract

: Dehydro-7,8-aryl-himachalene is a desired natural benzocycloheptene sesquiterpene found in the essential oil of Atlas cedar (Cedrus atlantica) in minor quantities. Herein, we report a simple and environmentally benign synthesis of this molecule via the aromatization of himachalene mixture (the major constituent of the same oil). The synthesis of the desired compound has been achieved by iodine/DMSO-mediated aromatization. The synthesized product has been characterized using MS spectrometry and NMR spectroscopy data. The treatment of the himachalene mixture with iodine led to the formation of dehydro-7,8-arylhimachalene, along with other rearrangement products catalyzed by the hydroiodic acid formed in situ. The use of DMSO as a co-solvent enabled the elimination of the acid formed and the regeneration of iodine. The optimization of the reaction conditions led to the formation of the desired product with a good yield. The present study highlights the development of a simple and environmentally benign method for the synthesis of a natural benzocycloheptene-based sesquiterpenoid in large quantities in order to explore its biological and chemical properties.

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碘介导的绯红烯芳香化反应：脱氢-7,8-芳基桧烯的合成

:脱氢-7,8-芳基-himachalene 是一种理想的天然苯并环庚烯倍半萜，可在阿特拉斯雪松（Cedrus atlantica）精油中少量发现。在此，我们报告了通过芳香化紫苏烯混合物（同一种精油的主要成分）合成这种分子的简单而环保的方法。我们通过碘/二甲基亚砜介导的芳香化反应合成了所需的化合物。利用 MS 光谱和 NMR 光谱数据对合成产物进行了表征。用碘处理桧烯混合物可生成脱氢-7,8-芳基桧烯，以及在原位形成的氢碘酸催化下的其他重排产物。使用二甲基亚砜作为助溶剂可以消除形成的酸，并使碘再生。通过优化反应条件，生成了所需的产物，而且收率很高。本研究强调了开发一种简单且对环境无害的方法，用于大量合成天然苯并环庚烯类倍半萜，以探索其生物和化学特性。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Letters in Organic Chemistry 化学-有机化学

CiteScore

1.30

自引率

12.50%

发文量

135

审稿时长

7 months

期刊介绍： Aims & Scope Letters in Organic Chemistry publishes original letters (short articles), research articles, mini-reviews and thematic issues based on mini-reviews and short articles, in all areas of organic chemistry including synthesis, bioorganic, medicinal, natural products, organometallic, supramolecular, molecular recognition and physical organic chemistry. The emphasis is to publish quality papers rapidly by taking full advantage of latest technology for both submission and review of the manuscripts. The journal is an essential reading for all organic chemists belonging to both academia and industry.