183308-67-0

Upstream product

• 98-59-9 p-toluenesulfonyl chloride 
• 183308-75-0 ((2S,3S)-3-{(R)-3-(tert-Butyl-dimethyl-silanyloxy)-3-[(2R,5R)-5-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-tetrahydro-furan-2-yl]-propyl}-oxiranyl)-methanol 
• 183308-64-7 Toluene-4-sulfonic acid (R)-2-hydroxy-2-[(2R,5R)-5-((S)-2-oxo-[1,3]dioxolan-4-yl)-tetrahydro-furan-2-yl]-ethyl ester 
• 183308-66-9 (R)-6-(tert-Butyl-dimethyl-silanyloxy)-6-[(2R,5R)-5-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-tetrahydro-furan-2-yl]-hex-2-yn-1-ol 
• 183308-76-1 (E)-(R)-6-(tert-Butyl-dimethyl-silanyloxy)-6-[(2R,5R)-5-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-tetrahydro-furan-2-yl]-hex-2-en-1-ol 
• 183308-65-8 (S)-2,2-Dimethyl-4-((2R,5R)-(R)-5-oxiranyl-tetrahydro-furan-2-yl)-[1,3]dioxolane 
• 69739-34-0 t-butyldimethylsiyl triflate 

Relevant academic research and scientific papers

The first total synthesis of 15-epi-annonin I

The first total synthesis of the 15-epimer 1b of the naturally occurring acetogenin annonin I 1a is described. All stereogenic centres in the bis-THF subunit are controlled via successive Sharpless asymmetric epoxidations (AE). Alkyl side chains were attached directly to the core using alkyne-epoxide couplings.