91898-18-9Relevant academic research and scientific papers
Total Synthesis of (+)-Cornexistin
Barber, David M.,Magauer, Thomas,Steinborn, Christian,Wildermuth, Raphael E.
supporting information, p. 17282 - 17285 (2020/08/21)
Herein, we describe the first total synthesis of (+)-cornexistin as well as its 8-epi-isomer starting from malic acid. The robust and scalable route features a Nozaki–Hiyama–Kishi reaction, an auxiliary-controlled syn-Evans-aldol reaction, and a highly efficient intramolecular alkylation to form the nine-membered carbocycle. The delicate maleic anhydride moiety of the nonadride skeleton was constructed from a β-keto nitrile. The developed route enabled the synthesis of 165 mg (+)-cornexistin.
Lewis acid-promoted addition of 1,3-bis(silyl)propenes to aldehydes: A route to 1,3-dienes
Borg, Tessie,Tuzina, Pavel,Somfai, Peter
experimental part, p. 8070 - 8075 (2011/11/28)
The Lewis acid-promoted addition of 1,3-bis(silyl)-propenes to aldehydes to provide the corresponding (E)-1,3-dienes in excellent stereoselectivity and good to excellent yields is reported. The procedure is mild, base-free, and operationally straightforward.
Selective cleavage of acetals with ZnBr2 in dichloromethane
Ribes, Celia,Falomir, Eva,Murga, Juan
, p. 1239 - 1244 (2007/10/03)
A selective cleavage of acetals of 1,2- and 1,3-diols has been achieved under mild conditions using ZnBr2 in dichloromethane at room temperature. Acetal types cleavable by this procedure include benzylidene, isopropylidene and cyclohexylidene acetals. This method is compatible with several other types of hydroxyl protecting groups such as Bn, Bz, TBDPS, TIPS and TBDMS.
Dimethylboron Bromide and Diphenylboron Bromide: Cleavage of Acetals and Ketals
Guindon, Yvan,Yoakim, Christiane,Morton, Howard E.
, p. 3912 - 3920 (2007/10/02)
The cleavage of various acetal and ketal derivatives by the use of dialkyl- and diarylboron halides is described.Acetals and ketals readily react with dimethylboron bromide or diphenylboron bromide at -78 deg C to give the corresponding carbonyl compounds in excellent yield.Under similar reaction conditions MEM, MOM, and MTM ethers are smoothly converted to alcohols.Acetonides are also cleaved with dimethylboron bromide while THP and THF ethers and methyl glycosides react at room temperature.Mechanistic considerations of the cleavage reactions are presented.The chemoselective virtues of dimethylboron bromide are summarized.
REGIOSELECTIVITY OF THE REACTIONS OF TRIALKYLALUMINUM REAGENTS WITH 2,3-EPOXYALCOHOLS: APPLICATION TO THE SYNTHESIS OF α-CHIRAL ALDEHYDES
Roush, William R.,Adam, Michael A.,Peseckis, Steven M.
, p. 1377 - 1380 (2007/10/02)
Treatment of optically active 2,3-epoxyalcohols with trialkylaluminum reagents followed by periodate cleavage constitutes a convenient synthesis of α-chiral aldehyde derivatives, especially when the branching alkyl group is methyl.
