1303501-13-4

Upstream product

• 120743-99-9 p-[(tert-butyldimethylsilyl)oxy]benzaldehyde 
• 522602-18-2 ethyl 3-(4-((tert-butyl(dimethyl)silyl)oxy)phenyl)propanoate 
• 123-08-0 4-hydroxy-benzaldehyde 
• 1421598-67-5 (+)-(3S,7S)-1,9-bis(4-(tert-butyldimethylsilyloxy)phenyl)-3,7-dihydroxynonan-5-one 
• 183140-16-1 C₁₇H₂₆O₃Si 
• 147974-20-7 3-[4-(tert-butyl-dimethyl-silanyloxy)phenyl]propionaldehyde 
• 622397-33-5 (S)-1-(4-((tert-butyldimethylsilyl)oxy)phenyl)hex-5-en-3-ol 
• 1421598-63-1 C₂₆H₃₈O₃Si 
• 1421598-64-2 C₂₆H₃₈O₄Si 
• 1425335-01-8 ericanone 3-O-β-D-xylopyranoside 

Relevant academic research and scientific papers

Concise Asymmetric Construction of C2-symmetric 1,9-Diarylnonanoids Using a Hypervalent Silicon Complex: Total Synthesis of (-)-Ericanone

By using a phosphine oxide-catalyzed enantioselective double aldol reaction, we achieved the concise construction of C2-symmetric 1,9-diarylnonanoids, enabling the synthesis of (-)-ericanone from p-hydroxybenzaldehyde in 6 steps with 65 % overall yield. The enantioselective double aldol reaction is useful for establishing C2-symmetric 1,9-diaryl-3,7-dihydroxy-5-nonanones with a single operation. Furthermore, the use of o-nosyl-protected p-hydroxybenzaldehyde and a 4,4′-disubstituted BINAP dioxide catalyst dramatically improved the reactivity and selectivity in the double aldol reaction, enabling the total synthesis of (-)-ericanone with high yield and with excellent enantiopurity.

Enantioselective total synthesis of (-)-ericanone

The first total synthesis of (-)-ericanone was achieved in 10 steps with a 16% overall yield from p-hydroxybenzaldehyde. Notable features of this stereocontrolled approach include a Keck allylation to install the stereocenter at C3 and a 1,5-anti aldol reaction to install the hydroxyl group at C7.

Three further 1,9-diarylnonanoid 3-O-glycosides from Erica cinerea

In addition to the six diarylnonanoids and diarylnonanoid 3-O-glucosides previously reported from Erica cinerea, the multistep chromatographic processing of the acetone extract of the fresh aerial parts resulted in the isolation of three more representatives as glycosides derived from either (-)-ericanone or (-)-α-ericadione. From the spectroscopic data, the new structures were elucidated as (-)-(3S,7S)-ericanone 3-O-β-d-xylopyranoside, (-)-(3S,7S)-3″-hydroxyericanone 3-O-β-d-glucopyranoside, and (-)-(3S)-3″-hydroxy-α-ericadione 3-O-β-d-glucopyranoside respectively. In the 1H and 13C NMR spectra run in CD 3OD, the latter metabolite was as (-)-α-ericadione 3-O-β-d-glucopyranoside, also found as a permanent mixture of the major s-trans (70%) and the minor s-cis (30%) conformers. Such result - in connection with the protic solvent - seems to have never been reported earlier for α-alkadiones. Moreover, mild acid hydrolysis of such a glucoside led directly to the 3,4-dehydrated aglycone moiety accompanied by its 6,7-dehydrated tautomer, according to two successive dehydrations of the anticipated aglycone. Furthermore, although missing in this species, the postulated β-ericadione continues to be regarded as an essential intermediate at the crossroads of the biogenesis of most of the E. cinerea 1,9-diarylnonanoids.