A novel one-step synthesis of alkenylated 1,4-benzoquinone natural products
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1
College of William & Mary, United States
Naturally occurring quinones have widely exhibited therapeutic properties due to their bioactivity. In this work, we present a short and efficient one-step synthesis of benzoquinone derivatives based on alkenylation of 2-methyl-1,4-benzoquinone. An alkene side chain was introduced at C-6 and/or C-5 position, from the corresponding alkenylated bromide under zinc catalyst. Synthesized natural products 1a, 1b, and 2 were confirmed by 1H and 13C NMR spectroscopy and 1,1-ADEQUATE experiment.
Acknowledgements
We wish to express our thanks to William & Mary Charles Center and Chemistry Department for funding support.
Keywords:
Natural products (NPs),
Quinone (C6H 4O2),
1,4-benzoquinone (BZQ),
one-step synthesis,
Alkenylations,
Concise synthesis,
Biochemistry,
Organic synthesis and medicinal chemistry,
Ubiquinone derivatives
Conference:
National Organization for the Professional Advancement of Black Chemists and Chemical Engineers (NOBCChE) 45th Annual Conference , Orlando, Florida, United States, 17 Sep - 20 Sep, 2018.
Presentation Type:
Poster Presentation
Topic:
Medicinal Chemistry
Citation:
Han
Z and
Lashley
D
(2019). A novel one-step synthesis of alkenylated 1,4-benzoquinone natural products.
Front. Chem.
Conference Abstract:
National Organization for the Professional Advancement of Black Chemists and Chemical Engineers (NOBCChE) 45th Annual Conference .
doi: 10.3389/conf.fchem.2018.01.00001
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Received:
02 Oct 2018;
Published Online:
17 Jan 2019.
*
Correspondence:
Dr. Dana Lashley, College of William & Mary, Williamsburg, United States, dlashley@wm.edu