683746-82-9

Upstream product

• 98-09-9 benzenesulfonyl chloride 
• 13493-50-0 4-hydroxybenzaldehyde benzenesulfonate ester 
• 123-08-0 4-hydroxy-benzaldehyde 
• 501-97-3 4-hydroxyphenylpropionic acid 
• 31770-76-0 3-(4-hydroxyphenyl)propionic acid benzyl ester 

Downstream Products

• 1429416-48-7 (S,E)-1-(4’-(benzenesulfoxy)phenyl)-3-(tertbutyldimethyl)silyloxyhept-5-ene 
• 1429416-49-8 (S)-5-(4'-benzenesulfoxyphenyl)-3-(tertbutyldimethylsilyloxy)pentanal 
• 1429416-52-3 (5S,2E)-5-(tert-butyldimethyl)silyloxy-1,7-di(4’-(benzenesulfoxy))phenylhept-2-en-1-one 
• 1429416-53-4 (5S,2E)-3-(4’-benzenesulfoxyphenyl)ethynyl-5-(tert-butyldimethyl)silyloxy-1,7-di(4’-(benzenesulfoxy))phenylheptanone 
• 1429416-47-6 (S,E)-1-(4’-benzenesulfoxyphenyl)hept-5-en-3-ol 

Relevant academic research and scientific papers

Synthesis of tetrahydropyranyl diarylheptanoids from Dioscorea villosa

Concise syntheses of four tetrahydropyranyl diarylheptanoids isolated from Dioscorea villosa have been described. The key features include Prins cyclization to construct the tetrahydropyran cores, Keck asymmetric allylation, and Mitsunobu inversion. Optimization of the Prins cyclization conditions in order to minimize racemization has been described. Our syntheses also confirmed the absolute stereochemistry of the natural products.

Total synthesis of (-)-blepharocalyxin D and analogues

An efficient strategy for the total synthesis of (-)-blepharocalyxin D and an analogue is described. The key step involves an acid-mediated cascade process in which reaction of methyl 3,3-dimethoxypropanoate with γ,δ- unsaturated alcohols possessing diastereotopic styrenyl groups gives trans-fused bicyclic lactones with the creation of two rings and four stereocenters in one pot.