160805-40-3

Upstream product

• 195517-63-6 2-[(2R,3R,6S)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-2-(2,2-dimethoxy-ethyl)-3,6-dihydro-2H-pyran-3-yl]-propionic acid methyl ester 
• 158780-35-9 (2R,3R,6R)-6-Allyl-2-hydroxymethyl-3,6-dihydro-2H-pyran-3-ol 
• 4098-06-0 triacetyl-D-galactal 
• 195517-62-5 2-[(2R,3R,6S)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-2-(2-oxo-ethyl)-3,6-dihydro-2H-pyran-3-yl]-propionic acid methyl ester 
• 160805-34-5 2-[(2R,3R,6S)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-2-(2,2-dimethoxy-ethyl)-3,6-dihydro-2H-pyran-3-yl]-propionaldehyde 
• 195517-61-4 2-[(2R,3R,6S)-2-Allyl-6-(tert-butyl-dimethyl-silanyloxymethyl)-3,6-dihydro-2H-pyran-3-yl]-propionic acid methyl ester 
• 195517-60-3 Propionic acid (2R,3R,6R)-6-allyl-2-(tert-butyl-dimethyl-silanyloxymethyl)-3,6-dihydro-2H-pyran-3-yl ester 
• 195517-59-0 (2R,3R,6R)-6-allyl-2-[(tert-butyldimethylsilanyloxy)methyl]-3-hydroxy-3,6-dihydro-2H-pyran 
• 129230-32-6 3-(4',6'-di-O-acetyl-2',3'-dideoxy-α-D-threo-hex-2'-enopyranosyl)-1-propene 

Relevant academic research and scientific papers

A Synthetic Approach to the Tricyclic System of Forskolin from D-Galactose

The synthesis of the tricyclic system of forskolin by an intramolecular Diels-Alder reaction is described, starting from tri-O-acetyl-D-galactal.

A New Synthetic Approach to Forskolin: Construction of the ABC Ring System from D-Galactose

Intramolecular Diels-Alder reaction of dienyne 14 afforded naphthopyran 18 which underwent 1,4-addition of methyl copper reagent to give the functionalized tricyclic system of forskolin 17. The synthesis of dienyne 14 is based on a stereoselective introduction of carbon side chains at C(1) and C(2) of tri-O-acetyl-D-galactal via C-Ferrier followed by Claisen-Ireland rearrangements.