16247-35-1

Upstream product

• 60-29-7 diethyl ether 
• 464-49-3 (1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one 
• 13139-86-1 4-methoxyphenyl magnesium bromide 
• 736109-58-3 1,7,7-trimethyl-bicyclo[2.2.1]heptan-2-one 
• 76-22-2 Camphor 
• 578006-87-8 (1R,2S,4R)-2-(4-methoxyphenyl)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol 

Downstream Products

• 63785-90-0 p-Bornylanisol 
• 4488-58-8 4-(1,7,7-trimethylbicyclo[2.2.1]hept-exo-2-yl)phenol 

Relevant academic research and scientific papers

Synthesis of Simplified Azasordarin Analogs as Potential Antifungal Agents

A new series of simplified azasordarin analogs was synthesized using as key steps a Diels-Alder reaction to generate a highly substituted bicyclo[2.2.1]heptane core, followed by a subsequent nitrile alkylation. Several additional strategies were investigated for the generation of the key tertiary nitrile or aldehyde thought to be required for inhibition at the fungal protein eukaryotic elongation factor 2. This new series also features a morpholino glycone previously reported in semisynthetic sordarin derivatives with broad spectrum antifungal activity. Despite a lack of activity against Candida albicans for these early de novo analogs, the synthetic route reported here permits more comprehensive modifications of the bicyclic core and structure-activity relationship studies that were not heretofore possible.

Stereo- and regioselectivity in dynamic gas-phase thermoisomerization (DGPTI): Novel route to α-campholanic acid and derivatives

(Matrix presented) Dynamic gas-phase thermoisomerization (DGPTI) of (-)-2-phenylisoborneols effects stereo- and regioselective ring opening under formation of (+)-trans-α-campholanic acid derivatives. Similarly, (-)-α-2-phenylfenchol underwent under DGPTI conditions ring opening to (-)-fencholic acid derivatives. In both cases, DGPTI led to cleavage of the weakest bond in the isomeric bicyclic structures. A reaction mechanism involving a diradical intermediate is supported by a deuterium labeling study.