Orbit Natural Product Derivatives
Orbit Natural Product Derivatives
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Research

Below are some examples of our research in methodology and natural product synthesis. NOTE: This content is intended for educational or entertainment purposes only. Many of the chemicals used are hazardous and should only be handled by those (adult) individuals who are properly trained in the art.

Studies directed toward the synthesis of Berberine (RouteA)

These pdfs illustrate some experiments performed according to our first route to an intermediate used in a published total synthesis of Berberine (a benzylisoquinoline alkaloid natural product). Berberine (ie. Berberis aristata) has a long history of use in Ayurvedic and traditional Chinese medicine. Please note our Berberine synthesis is a long term project for which we’ll carry out and post new experiments as time and funding permits.

Chloromethylation of 1,3-Benzodioxole (Conditions A)_062224 (pdf)Download
Grignard Reaction to MDPAA (Route A)_070724 (pdf)Download

Demethylation of Eugenol: Synthesis of Hydroxychavicol

We found that by first converting Eugenol to its borate ester, it is activated as an electrophile toward a variety of demethylating agents including alkali halide salts and sulfur nucleophiles. Hydroxychavicol, a natural product found in betel leaves (Piper betle), is a unique aroma compound with a smoky odor. Interestingly, it is a common (and often spiritual) practice for people to chew betel leaves (and nuts) in some regions of India and south Asia.

Demethylation_of_Eugenol_120624_TEB_KI_DMF (pdf)Download

Aldol condensation: Aryl aldehyde + glycol acetal

After accidentally preparing 2-methyl-1,3-dioxolane in an intended 1,4-dioxane synthesis, we discovered conditions under which some simple glycol acetals could be deprotected in situ and reacted with aromatic aldehydes to afford cinnamaldehyde derivatives in moderate yields.

Files coming soon.

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