181534-70-3

Upstream product

• 181534-67-8 (5R,6S)-6-[(1S,2R)-1-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-ethyl]-5-trimethylsilanyloxy-5,6-dihydro-pyran-2-one 
• 181534-74-7 Toluene-4-sulfonic acid (2S,3R)-2-[(1S,2R)-1-benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-ethyl]-6-oxo-3,6-dihydro-2H-pyran-3-yl ester 
• 181534-66-7 (R)-5-[(1R,2R,3R)-2-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-3-phenyl-1-trimethylsilanyloxy-propyl]-5H-furan-2-one 
• 181534-68-9 (5R,6R)-6-[(1S,2R)-1-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-ethyl]-5-hydroxy-5,6-dihydro-pyran-2-one 
• 153000-32-9 (R)-5-[(1R,2S,3R)-2-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-3-phenyl-propyl]-5H-furan-2-one 
• 181534-69-0 (2R,3R,3aR,7aS)-3-(benzyloxy)-2-phenyl-3,3a-dihydro-2H-furo[3,2-b]pyran-5(7aH)-one 

Downstream Products

• 139626-38-3 (4S,4aS,6R,7R,7aS)-4,7-dihydroxy-6-phenyl-1,5-dioxabicyclo[4.3.0]nonan-2-one 
• 139626-38-3 (2R,3R,3aS,7R,7aS)-3,7-dihydroxy-2-phenyltetrahydro-2H-furo[3,2-b]pyran-5(6H)-one 
• 181781-56-6 (-)-(1S,5S,6S,8R,9R)-9-benzyloxy-5-hydroxy-8-phenyl-2,7-dioxabicyclo[4.3.0]nonan-3-one 
• 194355-13-0 (2R,3R,3aS,7R,7aS)-3-Benzyloxy-5-methoxy-2-phenyl-hexahydro-furo[3,2-b]pyran-7-ol 
• 181534-71-4 (2R,3R,3aS,7R,7aS)-3-(benzyloxy)-7-hydroxy-2-phenyltetrahydro-2H-furo[3,2-b]pyran-5(6H)-one 

Relevant academic research and scientific papers

Stereoselective Syntheses of (+)-Goniotriol, (+)-8-Acetylgoniotriol, (+)-Goniodiol, (+)-9-Deoxygoniopypyrone, (+)-Altholactone, and (-)-Goniofupyrone

The γ-lactone intermediate (-)-7, derived from (+)-tricarbonyl(η6-o-(trimethylsilyl)benzaldehyde)chromium(0) complex, was efficiently converted into the corresponding δ-lactone intermediate (-)-11. This second intermediate has been shown to be a versatile compound for stereoselective syntheses of natural styryllactones possessing a six-membered lactone moiety, isolated from Goniothalamus giganteus, by transforming it into (+)-goniotriol, (+)-8-acetylgoniotriol, (+)-goniodiol, (+)-9-deoxygoniopypyrone, (+)-altholactone, and (-)-goniofupyrone.

First total synthesis and structural elucidation of (-)-goniofupyrone

The first total synthesis of (-)-goniofupyrone, isolated from Goniothalamus giganteus, was accomplished in a stereoselective manner from (+)-tricarbonyl(η6-2-trimethylsilylbenzaldehyde)chromium(0) complex. This synthesis unambiguously established the relative and absolute stereochemistry of (-)-goniofupyrone.