853784-89-1Relevant academic research and scientific papers
Divergent synthesis of (6S,1′S,2′R)-hydroxypestalotin via tandem conjugate addition-lactonization sequence
Mallula, Venkata Satyanarayana,Srinivas, Batthula,Radha Krishna, Palakodety
supporting information, p. 1115 - 1117 (2015/02/19)
The stereoselective synthesis of (6S,1′S,2′R)-hydroxypestalotin from trans-hex-2-en-1-ol utilizing asymmetric dihydroxylation and Luche's reduction and tandem conjugative addition-lactonization as the key steps is reported.
Chemoenzymatic total synthesis of the phytotoxic lactone herbarumin III
Nanda, Samik
, p. 3661 - 3663 (2007/10/03)
Asymmetric total synthesis of phytotoxic nonenolide herbarumin III was accomplished by a chemoenzymatic approach. The main highlight of the synthesis was to fix the hydroxyl stereocenters (C7 and C9) by lipase catalyzed irreversible transesterification.
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.
