220482-19-9

Upstream product

• 34132-31-5 2-bromo-3-hydroxy-5-methoxytoluene 
• 220482-17-7 (-)-(2S,3R)-1,4-bis(benzyloxy)-3-(2-bromo-3-methoxy-5-methylphenyl)oxybutan-2-ol 
• 3209-13-0 O-methylorcinol 
• 220482-16-6 (-)-(2R,3S)-1,4-bis(benzyloxy)-2-(2-bromo-3-methoxy-5-methylphenyl)oxy-3-t-butyldimethylsilyloxybutane 
• 190782-47-9 (2S,3S)-1,4-bis(benzyloxy)-3-t-butyldimethylsilyloxybutan-2-ol 
• 17401-06-8 (2S,3S)-1,4-bis(benzyloxy)-2,3-butanediol 
• 36661-64-0 2-bromo-3-methoxy-5-methylphenol 
• 311313-44-7 2-(3-methoxy-5-methylphenoxy)tetrahydropyran 

Relevant academic research and scientific papers

Formal synthesis of both atropomers of desertorin C and an example of chirality transfer from a biphenyl axis to a spiro centre and its reverse

In connection with the synthesis of 4,4′,7,7′-tetramethoxy-5,5′-dimethyl-6,8′-bicoumarin (desertorin C) (11) in enantiopure form, the diastereomeric ratios of the products of the reactions between 2-isopropyloxy-6-methoxy-4-methylphenylmagnesium bromide (24) and (4S)-4-isopropyl-2-(2,3,5-trimethoxyphenyl)-4,5-dihydrooxazole (23), between 2,4-dimethoxy-6-methylphenylmagnesium bromide (37) and (4S)-4-isopropyl-2-(2,3-dimethoxy-5-methylphenyl)-4,5-dihydrooxazole (36), and between 2,4-dimethoxy-6-(t-butyldimethylsilyloxy)methylphenyl-magnesium bromide (46) and the oxazole (36) were explored. The major product of the last mentioned reaction was converted into (S,4S)-4-isopropyl-2-(2′-hydroxymethyl-4′,6,6′-trimethoxy-4- methyl-1,1′-biphenyl-6-yl)-4,5-dihydroxazole (49), the axial configuration of which was confirmed by single crystal X-ray structural determination. The similar product (S,4S)-2-(2′,4′,6-trimethoxy-4,6′-dimethyl-1,1′- biphenyl-6-yl)-4,5-dihydrooxazole (43) was converted into (S)-1-(2,4′,6′-trimethoxy-4,6′-biphenyl-2-yl)ethanone (57) which furnished (S)-1-(2′,4′,6-trimethoxy-4,6′-dimethyl-1,1′-biphenyl-2- yl)acetamide (58) (43%) and (S)-2,7′-dimethoxy-3′,5′,6-trimethylspiro[cyclohexa-2,5-diene- 1,1′-(1H)isoindole]-4-one (61) (30%) on Schmidt rearrangement. The dienone (61) on reduction and methylation regenerated the ketone (57). The methodology of Lipschutz was adapted for the synthesis of both enantiomers of 1,1′-(2′,4-dihydroxy-6,6′-dimethoxy-2,4′- dimethylbiphenyl-3,3′-diyl)bisethanone (32) and (83) which constitutes a formal synthesis of both enantiomers of desertorin C. CSIRO 2000.

A formal synthesis of both atropenantiomers of desertorin C

Asymmetric synthesis of both enantiomers of 1,1'-(2',4-dihydroxy-6,6'-dimethoxy-2,4'-dimethylbiphenyl-3,3'-diyl) -bisethanone allows the formal synthesis of both enantiomers of 4,4',7,7'-tetramethoxy-5,5'-dimethyl-6,8'- bicoumarin (desertorin C).