883994-35-2

Upstream product

• 883898-44-0 (4R,6R,7E,10S,11E)-4-(tert-butyldimethyl)silylperoxy-12-phenyl-4,6,10-trimethyldodeca-7,11-dien-2-ol 
• 883898-45-1 (3R)-3,5-dimethyl-3-[(2R,3E,6S,7E)-2,6-dimethyl-8-phenyl-octa-3,7-dienyl]-5-(2-methoxyethoxy)-1,2-dioxolane 
• 883898-16-6 (2S,4R,6R,7E,10S,11E)-4,6,10-trimethyl-12-phenyldodeca-7,11-diene-2,4-diol 
• 883898-40-6 (2R,4R,6R,7E,10S,11E)-4-hydroperoxy-12-phenyl-4,6,10-trimethyldodeca-7,11-dien-2-ol 
• 883898-39-3 (2R,3R,4R,6R,7E,10S,11E)-3,4-epoxy-4,6,10-trimethyl-12-phenyldodeca-7,11-dien-2-ol 
• 883898-15-5 (2S,3R,4R,6R,7E,10S,11E)-3,4-epoxy-4,6,10-trimethyl-12-phenyldodeca-7,11-dien-2-ol 
• 883898-14-4 (2R,3R,5R,6E,9S,10E)-2,3-epoxy-3,5,9-trimethyl-11-phenylundeca-6,10-dien-1-ol 
• 883898-18-8 (2R,4R)-2-[(2R,3E,6S,7E)-2,6-dimethyl-8-phenylocta-3,7-dienyl]-2,4-dimethyloxetane 
• 883898-38-2 (2S,3R)-3-((3E,7E)-(2R,6S)-2,6-Dimethyl-8-phenyl-octa-3,7-dienyl)-3-methyl-oxirane-2-carbaldehyde 
• 883898-46-2 (5R)-3,5-dimethyl-5-[(2R,3E,6S,7E)-2,6-dimethyl-8-phenyl-octa-3,7-dienyl]-1,2-dioxolane-3-acetic acid ethyl thioester 
• 67-56-1 methanol 

Relevant academic research and scientific papers

Asymmetric synthesis of 1,2-dioxolane-3-acetic acids: Synthesis and configurational assignment of plakinic acid A

The first asymmetric synthesis of 1,2-dioxolane-3-acetic acids is reported. Key features include the stereoselective opening of enantiomerically enriched oxetanes by hydrogen peroxide, conversion of the resulting 4-hydroperoxy-2- alkanols to 3-alkoxy-1,2-dioxolanes, and Lewis acid mediated homologation of the latter with a thioester silyl ketene acetal. The approach is modeled on 3,5-dimethyl-5-hexadecyl-1,2-dioxolane-3-acetic acid (1a), an unnamed natural product, and an optimized strategy is applied to the synthesis of four stereoisomers of plakinic acid A (2), allowing a configurational assignment of this incompletely characterized natural product.