1027086-66-3

Upstream product

• 90965-06-3 dimethyl 1-(1-diazo-2-oxopropyl)phosphonate 
• 132969-60-9 (2S)-3-[(4-methoxybenzyl)oxy]-2-methylpropanal 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 89238-99-3 O-(4-methoxybenzyl)-trichloroacetimidate 
• 136320-64-4 (2R)-3-[(4-methoxybenzyl)oxy]-2-methylpropanol 
• 132969-71-2 methyl (2S)-[(4-methoxybenzyl)oxy]-2-methylpropanoate 

Downstream Products

• 1027086-68-5 (5S,6S,E)-methyl 3-((R)-4-(4-methoxybenzyloxy)-3-methylbut-1-ynyl)-6-(tert-butyldimethylsilyloxy)-5-hydroxy-9-(trimethylsilyl)non-2-en-8-ynoate 
• 1046471-27-5 (R,E)-1-(((4-iodo-2-methylbut-3-en-1-yl)oxy)methyl)-4-methoxybenzene 
• 1591271-07-6 (S)-1-(((3-iodo-2-methylbut-3-en-1-yl)oxy)methyl)-4-methoxybenzene 
• 1591271-09-8 (1R,2S,3S,4R)-2-(2-((tert-butyldimethylsilyl)oxy)ethyl)-1-((R)-4-((4-methoxybenzyl)oxy)-3-methylbut-1-en-2-yl)-4-methyl-3-((triisopropylsilyl)oxy)cyclopentan-1-ol 
• 1591271-10-1 (1S,2S,3S,4R)-2-(2-((tert-butyldimethylsilyl)oxy)ethyl)-1-((R)-4-((4-methoxybenzyl)oxy)-3-methylbut-1-en-2-yl)-4-methyl-3-((triisopropylsilyl)oxy)cyclopentan-1-ol 
• 1591271-13-4 (1R,2S,3S,4R)-2-(2-((tert-butyldimethylsilyl)oxy)ethyl)-1-((1S,2S)-1-hydroxy-3-((4-methoxybenzyl)oxy)-2-methylpropyl)-4-methyl-3-((triisopropylsilyl)oxy)cyclopentan-1-ol 
• 1591271-14-5 (1R,2S,3S,4R)-2-(2-((tert-butyldimethylsilyl)oxy)ethyl)-1-((1R,2S)-1-hydroxy-3-((4-methoxybenzyl)oxy)-2-methylpropyl)-4-methyl-3-((triisopropylsilyl)oxy)cyclopentan-1-ol 
• 1591271-15-6 triisopropyl(((4S,5R,6S,7S,8R)-4-((S)-1-((4-methoxybenzyl)oxy)propan-2-yl)-6-(2-((2-methoxypropan-2-yl)oxy)ethyl)-2,2,8-trimethyl-1,3-dioxaspiro[4.4]nonan-7-yl)oxy)silane 
• 1591271-08-7 (R)-2-(4-((4-methoxybenzyl)oxy)-3-methylbut-1-en-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 

Relevant academic research and scientific papers

Jatrophane diterpenes: Preparation of the western fragment of pl-3

Jatrophane diterpenes are structurally intriguing natural products with promising biological properties. Herein, the synthesis of the western fragment of the Euphorbiaceae constituent Pl-3 starting from (1R,5S)-bicyclo[3.2.0]hept- 2-en-6-one is described. Key steps in the sequence include a Baeyer-Villiger oxidation, an iodolactonization reaction, and the installation of the northern side chain through the addition of a lithiated vinyl bromide. The overall efficiency of the route is increased by taking advantage of latent symmetry. The synthesis of the western fragment of Pl-3 is developed by taking advantage of the latent symmetry in an intermediate; both enantiomers are thus converted into the desired substrate. Key steps of the synthesis include a Baeyer-Villiger oxidation, an iodolactonization reaction, and the addition of a vinyllithium species to the completed cyclopentane moiety of the natural product.

Toward the synthesis of didemnaketal B: A convergent synthesis of the C9-C28 subunit

(Chemical Equation Presented) Synthesis of the C9-C28 subunit of didemnaketal B has been developed. This subunit was convergently prepared from four chiral synthons and at the longest linear sequence required 16 steps.

Coupling of alkenes and alkynes: Synthesis of the C1-C11 and C18-C28 fragments of miyakolide

A transition metal-mediated, atom-economical approach toward the crucial A and D rings of miyakolide is described. A Pd-catalyzed alkyne-alkyne coupling/6-endo-dig cyclization is employed to assemble the A ring fragment. The key D ring pyran is constructed utilizing an Ru-catalyzed alkene-alkyne coupling followed by a Pd-catalyzed allylic alkylation to establish the all-cis stereochemistry.