618359-63-0

Upstream product

• 905266-48-0 1-(4-(tert-butyldimethylsilyloxy)phenyl)prop-2-en-1-one 
• 1564249-20-2 (Z)-(4-(1-(9-borabicyclo[3.3.1]nonan-9-yloxy)prop-1-enyl)phenoxy)(tert-butyl)dimethylsilane 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 120743-99-9 p-[(tert-butyldimethylsilyl)oxy]benzaldehyde 
• 134136-83-7 1-(4-{[tert-butyl(dimethyl)silyl]oxy}phenyl)propan-1-one 

Downstream Products

• 618359-66-3 (2R,3R,4S,5S)-2,5-Bis-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-3,4-dimethyl-tetrahydro-furan 
• 130325-40-5 (2α,3β,4β,5α)-2,5-Bis(4-hydroxyphenyl)-3,4-dimethyltetrahydrofuran 

Relevant academic research and scientific papers

Synthesis and chiral HPLC analysis of the dibenzyltetrahydrofuran lignans, larreatricins, 8'-epi-larreatricins, 3,3'-didemethoxyverrucosins and meso-3,3'-didemethoxynectandrin B in the creosote bush (Larrea tridentata): evidence for regiospecific control of coupling.

The creosote bush (Larrea tridentata) lignans are linked via 8-8' bonds, with the simplest apparently being E-p-anol derived. Of the latter, four of the six theoretically possible diastereoisomers were isolated, namely (-)-larreatricin, (-)-8'-epi-larreatricin, meso-3,3'-didemethoxynectandrin B and the new compounds, (+)- and (-)-3,3'-didemethoxyverrucosins. Following synthesis of each in either racemic or meso form, and chiral HPLC separation of the antipodes of the racemates, it was established that naturally occurring (-)-larreatricin and (-)-8'-epi-larreatricin were present in 92 and 98% enantiomeric excess, respectively, whereas 3,3'-didemethoxyverrucosin was essentially racemic and 3,3'-didemethoxynectandrin B was in the meso-form. The evidence suggests that formation of these lignans occurs under regiospecific, rather than stereoselective, coupling control. This contrasts with laccase-catalyzed "random" coupling of E-p-anol in vitro which generates the corresponding racemic 8-8', 8-3' and 8-O-4' linked dimeric moieties.

Oxovanadium(v)-induced diastereoselective oxidative homocoupling of boron enolates

Oxovanadium(v)-induced dl-selective oxidative coupling of (Z)-boron enolate was demonstrated to give the corresponding 2,3-disubstituted 1,4-diketone in a good yield. High selectivity (up to 94:6) was attained when the reaction was performed with VO(OPr-i)2Cl at -30 °C. The Royal Society of Chemistry 2014.