New method for preparing aroma sesquiterpene Commiphoranes C-D intermediate compound

Through the intramolecular free radical tandem cyclization reaction, the synthesis route of aromatic sesquiterpene Commiphoranes C–D intermediates is simplified, and the lengthy and high cost problems in the prior art are solved, and the intermediates of such compounds are efficiently prepared, which is suitable for industrial production.

CN120349296APending Publication Date: 2025-07-22SOUTHWEST JIAOTONG UNIV
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Patent Information

Application Number
CN202510502748.X
Authority / Receiving Office
CN · China
Patent Type
Applications(China)
Current Assignee / Owner
Filing Date
2025-04-22
Publication Date
2025-07-22

AI Technical Summary

Technical Problem

In the prior art, the synthetic route of aromatic sesquiterpenes Commiphoranes C-D is lengthy, the reagents are expensive and the yield is low, making it difficult to efficiently prepare intermediates of such compounds.

Method used

Intramolecular free radical tandem cyclization reaction was adopted, and the aromatic sesquiterpene of Commiphorane Commiphoranes C–D intermediate was synthesized by tandem cyclization of n-butyl lithium and diiodoethane, demethoxyl of boron tribromide, nucleophilic substitution of 3-allyl bromine and potassium carbonate, format reaction and oxidation of Dess-Martin oxidizer. Finally, intramolecular free radical tandem cyclization was used for intramolecular free radicals to synthesize the aromatic sesquiterpene Commiphoranes C–D intermediate.

Benefits of technology

It simplifies the synthesis steps, reduces costs, increases yield, is suitable for industrial production, and has strong promotion potential.

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Abstract

The invention provides a novel method for preparing an intermediate compound of aromatic sesquiterpenes Commiphoranes C-D. The method comprises the following steps: substituting the ortho-position of a compound 1 with iodine through n-butyllithium and diiodoethane to obtain a compound 2; removing methoxyl by using boron tribromide to obtain a compound 3; performing nucleophilic substitution on 3-allyl bromide and potassium carbonate to synthesize a compound 4; carrying out Grignard reaction to obtain a compound 5; oxidizing into a compound 6 through a Dess-Martin oxidizing agent; finally, (CH3Si) 3SiH and triethyl boron are subjected to intramolecular free radical series cyclization, so that synthesis of an aromatic sesquiterpene Commiphoranes C-D intermediate compound is successfully completed, sufficient preparation is made for follow-up total synthesis of the natural product, key intramolecular free radical series cyclization has the capacity of efficiently constructing a polycyclic system, and the synthesis process is simple and convenient. According to the preparation method, the defects of expensive reagents, long 14-step linear synthesis route, low yield and the like in the existing synthesis route are overcome; the popularization potential is high.
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