280758-01-2Relevant articles and documents
Stereoselective total synthesis of tubulysin v
Wang, Rui,Tian, Ping,Lin, Guoqiang
, p. 40 - 48 (2013/08/24)
The total synthesis of tubulysin V was accomplished in 1.0% overall yield with linear 13 steps. Our synthetic strategy featured the following two reactions. One is zinc-mediated aza-Barbier reaction of (R)-N-tert- butanesulfinyl imine 8 with β-ester group functionalized allylic bromide 9 to afford the chiral homo-allylic amine (7); the other is to employ the methodology of aqueous indium-mediated aza-Barbier reaction previously developed by our group, giving the chiral homo-allylic amine 13 with high efficiency. The total synthesis of tubulysin V was accomplished in 1.0% overall yield with linear 13 steps. Our synthetic strategy featured the following two reactions. One is zinc-mediated aza-Barbier reaction of (R)-N-tert-butanesulfinyl imine 8 with β-ester group functionalized allylic bromide 9 to afford the chiral homo-allylic amine 7; the other is to employ the methodology of aqueous indium-mediated aza-Barbier reaction previously developed by our group, giving the chiral homo-allylic amine 13 with high efficiency. Copyright
Synthesis of homochiral N-Boc-β-aminoaldehydes from N-Boc-β-aminonitriles
Toujas, Jean-Louis,Jost, Eric,Vaultier, Michel
, p. 713 - 718 (2007/10/03)
Enantiopure N-Boc-β-aminoaldehydes are efficiently prepared in good yields from N-Boc-β-aminonitriles by reduction of the nitrile function with diisobutylaluminium hydride (DIBAL-H) - Keywords: β-aminoaldehyde; β-aminonitrile; α-aminoacid; homochiral; enantiomeric excess; reduction; DIBAL-H