42719-63-1

Upstream product

• 623-47-2 propynoic acid ethyl ester 
• 108-73-6 3,5-dihydroxyphenol 
• 5392-40-5 (E/Z)-3,7-dimethyl-2,6-octadienal 
• 42259-11-0 (+/-)-eriobrucinol acetate 
• 72646-85-6 5-Hydroxy-7-methoxy-2-methyl-2-(4-methyl-pent-3-enyl)-2H-chromene-6-carbaldehyde 
• 72646-86-7 Acetic acid 6-formyl-7-methoxy-2-methyl-2-(4-methyl-pent-3-enyl)-2H-chromen-5-yl ester 
• 2174-64-3 5-methoxyresorcinol 
• 3519-76-4 2,4-dihydroxy-6-methoxybenzaldehyde 
• 72646-88-9 C₁₉H₂₂O₅ 
• 72646-87-8 C₂₀H₂₄O₅ 

Relevant academic research and scientific papers

Total syntheses of cannabicyclol, clusiacyclol A and B, iso-eriobrucinol A and B, and eriobrucinol

Total syntheses of a series of chromane natural products that contain a cyclobutane ring are described. A unified theme in the strategy employed for all these syntheses is an oxa-[3 + 3] annulation for constructing the chromane nucleus and a stepwise cationic [2 + 2] cycloaddition for the cyclobutane formation. More importantly, the two reactions could be rendered in tandem, thereby providing an expeditious approach to this family of natural products.

Syntesis of (+/-)-Eriobrucinol and Regioisomeric Monoterpenoid Coumarins, using Intramolecular Cycloadditions

Unambiguous syntheses of the three regioisomers (8), (13), and (16), of the eriobrucinol structure, are reported.The (+/-)-cyclol (8) is spectrally identical with natural (-)-eriobrucinol from Eriostemon brucei, thus confirming Jefferies and Worth's structural proposal by synthesis.