5259-31-4Relevant academic research and scientific papers
A mild and chemoselective method for the deprotection of tert-butyldimethylsilyl (TBDMS) ethers using iron(III) tosylate as a catalyst
Bothwell, Jason M.,Angeles, Veronica V.,Carolan, James P.,Olson, Margaret E.,Mohan, Ram S.
supporting information; experimental part, p. 1056 - 1058 (2010/04/05)
The most common method for the deprotection of TBDMS ethers utilizes stoichiometric amounts of tetrabutylammonium fluoride, n-Bu4N+F- (TBAF), which is highly corrosive and toxic. We have developed a mild and chemoselective method for the deprotection of TBDMS, TES, and TIPS ethers using iron(III) tosylate as a catalyst. Phenolic TBDMS ethers, TBDPS ethers and the BOC group are not affected under these conditions. Iron(III) tosylate is an inexpensive, commercially available, and non-corrosive reagent.
A Total Synthesis of (+/-)-Faranal, the True Trail Pheromone of Pharaoh's Ant, Monomorium pharaonis
Knight, David W.,Ojhara, Bol
, p. 955 - 960 (2007/10/02)
A relatively short total synthesis of the true trail pheromone of Pharaoh's ant, (+/-)-faranal is reported.The carbon skeleton was assembled by a Wittig condensation between (Z)-6-methyloct-5-en-2-one (4) and the 5-carboxypentylphosphonium salt (15).The ketone (4) was prepared in 'one-pot' and in a stereoselective manner using vinyl cuprate chemistry, while the relative stereochemistry of the two methyl substituents in the phosphonium salt (15) was established by using the Diels-Alder adduct (16) of buta-1,3-diene and maleic anhydride, which, after reduction and oxidative cleavage of the resulting cis-1,2-dimethylcyclohex-4-ene (18), gave only meso-3,4-dimethyladipic acid (19); this in turn was converted into the salt (15) in six straight-forward steps.
