87729-25-7

Upstream product

• 87729-26-8 2-endo-<(Benzoyloxy)methyl>-6-endo-hydroxy-2-exo-methylbicyclo<2.2.1>heptane 
• 65-85-0 benzoic acid 
• 38335-10-3 (+/-)-3-methyl-hexahydro-3,5-methano-cyclopenta[b]furan-2-one 
• 87760-80-3 6-endo-Hydroxy-2-endo-(hydroxymethyl)-3-exo-methylbicyclo<2.2.1>heptane 
• 98-88-4 benzoyl chloride 
• 13432-80-9 (+/-)-6c-iodo-3-methyl-(3ar)-hexahydro-3,5-methano-cyclopenta[b]furan-2-one 
• 7167-29-5 methyl 2-exo-methylbicyclo[2.2.1]hept-5-ene-2-endo-carboxylate 

Relevant academic research and scientific papers

Rotational Selectivity in Cyclobutene Ring Openings. Model Studies Directed toward a Synthesis of Verrucarin A

The rotational selectivity in the opening of dissymmetric cyclobutenes to the corresponding dienes is described.In the opening of the monoesters of cis-3,4-cyclobutenedicarboxylic acid, an unusual solvent effect on the ring opening is noted.Switching from Me2SO to 1,2-dichloroethane leads to a 3:1 ratio of the (E,Z)-muconates, favoring the ester on the E double bond.The two isomers can be differentiated by 13C NMR spectroscopy in which the above isomer shows a Δδ for the α,α' carbons of only ca. 2.5 ppm but a Δδ of 5-6 ppm for the isomer having the ester on theZ double bond.Inclusion of the cyclobutene as part of a macrotriolide related to verrucarin A imparts conformational control on the rotational selectivity to favor the E,Z isomer corresponding to the natural products.These relatively simple models inhibit protein synthesis in a fashion reminiscent of the natural products.