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Preparation of 6-aminocyclohepta-2,4-dien-1-one Derivatives via Tricarbonyl(tropone)iron
Published on: August 12, 2019
A three-step route to a tricyclic steroid precursor
Douglass F Taber1, Ritesh B Sheth
1Department of Chemistry & Biochemistry, University of Delaware, Newark, Delaware 19716, USA. taberdf@udel.edu
The Journal of Organic Chemistry
|September 26, 2008
Summary
Researchers developed a three-step synthesis for 2-alkyl cyclohexenones, key organic intermediates. This method utilizes Wittig reactions and UV irradiation to create valuable compounds, including the estrone methyl ether core.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
Background:
- 2-Alkyl cyclohexenones are versatile building blocks in organic synthesis.
- Efficient synthetic routes to these compounds are crucial for accessing complex molecules.
Purpose of the Study:
- To develop a novel, efficient three-step synthesis for 2-alkyl cyclohexenones.
- To demonstrate the utility of this method in synthesizing the tricyclic core of estrone methyl ether.
Main Methods:
- Wittig reaction of aldehydes with (cyclopropylmethyl)triphenylphosphonium bromide to form alkenyl cyclopropanes.
- Photochemical rearrangement of alkenyl cyclopropanes to 2-substituted cyclohexenones via UV irradiation in the presence of iron carbonyl catalysts (Fe(CO)5).
Main Results:
- Successfully synthesized a series of 2-alkyl cyclohexenones.
- Achieved a three-step synthesis of the estrone methyl ether tricyclic core, showcasing the method's applicability.
Conclusions:
- The developed method provides an efficient route to 2-alkyl cyclohexenones.
- This synthetic strategy is valuable for constructing complex polycyclic structures like estrone methyl ether.
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