3475-39-6Relevant articles and documents
A Desymmetrization-Based Total Synthesis of Reserpine
Park, Jisook,Chen, David Y.-K.
supporting information, p. 16152 - 16156 (2018/11/23)
Reported herein is a desymmetrization-based synthetic approach to the fused polycyclic indole alkaloid reserpine. The centerpiece of the developed strategy features an internal desymmetrization process that enabled the use of a readily accessible and nonstereogenic reserpine E-ring precursor, in contrast to the synthesis-intensive and stereodefined E-ring intermediates employed in all past reserpine syntheses. Utilization of inexpensive reagents through an orchestrated sequence of carefully selected chemical transformations further highlight the overall effectiveness of the developed pathway.
SELECTIVE MONOBROMINATION OF KETONES BY BIS(DIMETHYLACETAMIDE)HYDROGEN TRIBROMIDE
Rodygin, M. Yu.,Mikhailov, V. A.,Savelova, V. A.
, p. 881 - 887 (2007/10/02)
A unified procedure for the α-monobromination of ketones by bis(dimethylacetamide)hydrogen tribromide in methanol is proposed.Methyl aryl ketones with donating and moderately accepting substituents in the ring readily enter into the reaction. 1-Bromo ketones are mostly formed during the bromination of methyl alkyl ketones.
SILYL- AND GERMYL-CYCLOPROPANONES
Zaitseva, G. S.,Krylova, G. S.,Perelygina, O. P.,Baukov, Yu. I.,Lutsenko, I. F.
, p. 1935 - 1947 (2007/10/02)
1.The reactions of silylcyclopropanones with compounds containing a mobile hydrogen atom and also with alkoxy, dialkylamino, and dialkoxyphosphinooxy derivatives of Group IVB elements give adducts at the carbonyl group of the cyclopropanone, and, when heated, these undergo isomerization with opening of the three-membered ring exclusively at the C1-C2 bond and with the formation of β-heteroelement-substituted propionic derivatives. 2.Acetic acid and bis(trifluoroacetic) anhydride in reaction with (trimethylsilyl)cyclopropanone form relatively stable products of addition at the carbonyl group. 3.Bromine and iodotrimethylsilane react with silylcyclopropanones with breakage of the C2-C3 bond of the cyclopropanone ring and give the corresponding O- and C-isomeric derivatives of α-silylated ketones containing halogen atoms in the molecule. 4.The reactions of silyl- and germyl-cyclopropanones with diazomethane and with azido-silanes and -germanes can provide a method of synthesis of heteroelement-substituted (Si, Ge) cyclobutanones and β-lactams.
