32526-16-2Relevant articles and documents
Total synthesis and complete structural assignment of Yaku'amide A
Kuranaga, Takefumi,Sesoko, Yusuke,Sakata, Komei,Maeda, Naoya,Hayata, Atsushi,Inoue, Masayuki
supporting information, p. 5467 - 5474 (2013/05/22)
Here we report the first total synthesis and the complete stereochemical assignment of yaku'amide A. Yaku'amide A (1) was isolated from a sponge Ceratopsion sp. as an extremely potent cytotoxin. Its structure was determined except for the C4-stereochemist
FeIII-catalyzed synthesis of primary amides from aldehydes
Gowda, Ravikumar R.,Chakraborty, Debashis
supporting information; experimental part, p. 2226 - 2229 (2011/06/17)
A direct synthetic route for the transformation of aldehydes into primary amides in the presence of catalytic amounts of FeCl3 in water is described. A direct synthetic route for the transformation of aldehydes into primary amides in the presence of catalytic amounts of FeCl3 in water is described. Copyright
Auxiliary chiral ketones in the asymmetric synthesis of α-amino acids by Strecker reaction
Bousquet, C.,Tadros, Z.,Tonnel, J.,Mion, J.,Taillades, J.
, p. 513 - 520 (2007/10/02)
The asymmetric synthesis of α-aminoamides 1 R1CH(CONH2)NH2 1 = Ph-CH2, 1b: R1 = Pri, 1c: R1 = Ph> that leads to the corresponding α-amino acids is achieved by a classical Strecker reaction 1CHO, HCN, NH3> using an auxiliary chiral ketone (R2R'2CO) as a catalyst.In the presence of an aqueous solution of HCN and NH3, the (-)-5R-(methylethenyl)-3R-cyano-2R-methylcyclohexanone 2(-) leads to the 5R-(methylethenyl)-3R-cyano-2R-methyl-1R-cyano-cyclohexylamine 3 with 80percent stereoselectivity.Following condensation with R1CHO, this α-aminonitrile R2R'2C(CN)NH2 3 yields the corresponding iminonitrile which undergoes a second asymmetric addition of HCN yielding an asymmetric α-aminodinitrile 4 R2R'2C(CN)-NH-CHR1(CN) with stereoselectivity that varies betweeen 62percent (R1 = Ph) and 79percent (R1 = Ph-CH2).The α-aminodinitrile obtained as the major product undergoes regioselective hydration of the secondary aminonitrile moiety followed by the decomposition ("retro-Strecker") of the tertiary aminonitrile moiety yielding an optically active α-aminoamide (eg 78percent optical purity for 1a) and the auxiliary chiral ketone 2 and ketonic derivatives.Keywords - α-aminonitrile / α-amino acid / asymmetric synthesis
