167777-55-1Relevant academic research and scientific papers
Total synthesis of halipeptin A, a potent anti-inflammatory cyclodepsipeptide from a marine sponge
Hara, Sousuke,Makino, Kazuishi,Hamada, Yasumasa
, p. 1081 - 1085 (2007/10/03)
Total synthesis of halipeptin A, a potent anti-inflammatory cyclodepsipeptide, was achieved through proline-catalyzed asymmetric α-oxidation, diastereoselective aldol reaction, silver cyanide-mediated esterification, and macrolactamization.
Total synthesis of (+)-pamamycin-607
Kang, Sung Ho,Jeong, Joon Won,Hwang, Yu Sang,Lee, Sung Bae
, p. 1392 - 1395 (2007/10/03)
Complete stereoselectivity was observed in the total synthesis of pamamycin-607 (1), which proceeded by iodoetherification of γ-triethylsilyloxyalkenes in the presence of an essential additive, silver carbonate, to provide the requisite three cis-2,5-disu
Synthesis of optically active β,γ-unsaturated α-amino acids of α,β-unsaturated γ-amino acids. S(N)2- vs. S(N)2'-dichotomy of the Mitsunobu amination of allylic alcohols
Mulzer,Funk
, p. 101 - 112 (2007/10/02)
Novel and efficient syntheses (6-9 steps, overall yields 10-30%) are described for optically pure β,γ-unsaturated α-amino acids and α,β-unsaturated γ-amino acids, starting from (R)-isopropylidene glyceraldehyde and ethyl (S)-lactate, respectively. The key step is the Mitsunobu reaction of chiral secondary allylic alcohols with phthalimide as the nucleophile, where α,γ allylic transpositions are observed for the first time. The structure-α,γ-ratio-relationship is studied and also the stereochemistry of the allylic transposition. The α-substitution proceeds via clean S(N)2 inversion, whereas the γ-substitution corresponds to an (E)-anti attack of the nucleophilic with varying stereoselectivities.
