91523-28-3Relevant articles and documents
Total synthesis of HUN-7293
Boger, Dale L.,Keim, Holger,Oberhauser, Berndt,Schreiner, Erwin P.,Foster, Carolyn A.
, p. 6197 - 6205 (1999)
The first total synthesis of the cyclic heptadepsipeptide HUN-7293 (1), a potent inhibitor of cell adhesion molecule expression exhibiting anti-inflammatory properties, is detailed. The most effective approach relied on an unusually efficient macrocyclization with the formation of the MLEU3 - LEU4 secondary amide that potentially benefits from intramolecular H-bonding preorganization of the acyclic substrate. The requisite linear depsipeptide was convergently assembled with the late stage introduction of the linking ester enlisting a Mitsunobu esterification that occurs with inversion of the DGCN α-center permitting the utilization of a readily available L-amino acid precursor to the D α-hydroxy carboxylic acid residue. An alternative and similarly attractive approach of direct macrolactonization of a substrate necessarily incorporating a D-DGCN subunit proved viable albeit less effective. Biological evaluation in cellular assays for vascular adhesion molecule expression confirmed that synthetic HUN-7923 (1) is essentially indistinguishable from the naturally occurring cyclodepsipeptide.
New 3-(hydroxybenzylidenyl)-indolin-2-ones
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, (2008/06/13)
The invention relates to a compound selected from those of formula (I): STR1 wherein R1, R2, R3, R4, R5 and X are as defined in the description, its Z and E isomers, its optical isomers, in pure form
A new synthesis of N-alkoxy-2-ethoxyarylacetamides from N-alkoxy-N-chloroarylacetamides with triethylamine in ethanol
Kikugawa,Shimada,Kato,Sakamoto
, p. 2192 - 2194 (2007/10/02)
Treatment of N-alkoxy-N-chloroarylacetamides with triethylamine in ethanol results in removal of a chlorine atom and introduction of an ethoxy group at the C-2 position of arylacetamides in moderate yields.
