355423-31-3

Upstream product

• 355423-49-3 5-(2,2-dimethyl-[1,3]dioxan-5-yl)-2-methyl-3-oxo-2-(3-oxo-pentyl)-pent-4-enoic acid methyl ester 
• 186581-53-3 diazomethane 
• 69841-90-3 4,8-dimethyl-1,5-dioxo-3-hydroxy-2-oxabicyclo<4.3.0>non-4(9)-ene 
• 548446-27-1 (S)-3-Hydroxy-4,7a-dimethyl-7,7a-dihydro-3H,6H-isobenzofuran-1,5-dione 
• 1629-58-9 4-penten-3-one 
• 102573-84-2 2,2-dimethyl-[1,3]dioxane-5-carbaldehyde 
• 355423-43-7 (E)-3-(2,2-Dimethyl-[1,3]dioxan-5-yl)-propenal 
• 355423-46-0 (E)-5-(2,2-Dimethyl-[1,3]dioxan-5-yl)-3-hydroxy-2-methyl-pent-4-enoic acid methyl ester 
• 355423-35-7 (E)-5-(2,2-Dimethyl-[1,3]dioxan-5-yl)-2-methyl-3-oxo-pent-4-enoic acid methyl ester 

Downstream Products

• 364330-78-9 4-(tert-butyl-dimethyl-silanyloxy)-2-[2-(2,2-dimethyl-[1,3]dioxan-5-yl)-vinyl]-1,3-dimethyl-cyclohexa-2,4-dienecarboxylic acid methyl ester 
• 364330-80-3 3-[(E)-2-(2,2-Dimethyl-[1,3]dioxan-5-yl)-vinyl]-4-hydroxymethyl-2,4-dimethyl-cyclohex-2-enone 
• 364330-79-0 {4-(tert-butyl-dimethyl-silanyloxy)-2-[2-(2,2-dimethyl-[1,3]dioxan-5-yl)-vinyl]-1,3-dimethyl-cyclohexa-2,4-dienyl}-methanol 

Relevant academic research and scientific papers

Studies on a new synthetic route towards cassiol

The synthesis of the acyclic intermediate 7 towards the preparation of cassiol (2) is described. The cyclization of 7 led to 5, a precursor of 2 and to the unexpected product 8.

Detours en route to a total synthesis of (+)-cassiol

A synthesis of the antiulcerogenic compound (+)-cassiol 1b has been achieved in 43% yield starting with lactol (S)-2 and sulfone 26. This short and efficient synthesis features the one-pot Julia olefination reaction of the sodium anion of (S)-2 with 26, through the key intermediate (-)-9. This synthesis has been developed as a result of exploratory experiments including different olefination reactions on 2. An attempt to synthesize the intermediate 9 by an intramolecular aldol condensation approach of the open chain precursor 4 is also described.

A concise synthesis of (+)-cassiol

A synthesis of the anti-ulcerogenic compound (+)-cassiol 1b with 43% overall yield has been achieved. This short and efficient synthesis features the one-pot Julia olefination reaction of lactol (S)-2 with sulfone 3b through the key intermediate (-)-4b.