669000-40-2

Upstream product

• 669000-33-3 methyl (5R,6E)-5-tert-butyldimethylsilyloxy-2-phenylsulfonyl-8-tetrahydro-2H-pyran-2-yloxy-6-octenoate 
• 669000-32-2 (3R,4E)-3-tert-butyldimethylsilyloxy-6-hydroxy-4-hexenyl 4-methylbenzenesulfonate 
• 157918-29-1 methyl (2E,4R)-4-<<(tert-butyl)dimethylsilyl>oxy>-6-hydroxyhex-2-eneoate 
• 669000-39-9 (E)-(R)-2-Benzenesulfonyl-5,8-dihydroxy-oct-6-enoic acid methyl ester 
• 669000-38-8 Toluene-4-sulfonic acid (E)-(R)-3-(tert-butyl-dimethyl-silanyloxy)-6-(tetrahydro-pyran-2-yloxy)-hex-4-enyl ester 
• 669000-37-7 (E)-(R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-(toluene-4-sulfonyloxy)-hex-2-enoic acid methyl ester 

Downstream Products

• 669000-29-7 (1R,4R,7R)-4-phenylsulfonyl-7-vinyl-2-oxabicyclo[2.2.1]heptan-3-one 
• 669000-30-0 ethyl (E)-3-(2R)-6-oxo-5-phenylsulfonyltetrahydro-2H-pyran-2-yl-2-propenyl carbonate 

Relevant academic research and scientific papers

Asymmetric Total Synthesis of Bacillariolide III, a Marine Oxylipin

(Matrix presented) The asymmetric total synthesis of bacillariolide III has been achieved via 15 linear steps in 14.6% overall yield. The key feature of this synthetic route involves the highly stereoselective construction of the vinyl-substituted bicyclic lactone by an intramolecular Pd(0)-catalyzed allylic alkylation and its facile conversion to the hydroxy bicyclic lactone skeleton of bacillariolide III, induced by stereoselective vinylcerium addition to the aldehyde. In addition, the (Z)-pentenoic acid was efficiently introduced by the internal hydroxy group tethered ring-closing metathesis (RCM).