TY - JOUR
T1 - The diastereoselective asymmetric total synthesis of NG-391, a neuronal cell-protecting molecule
AU - Hayashi, Yujiro
AU - Yamaguchi, Junichiro
AU - Shoji, Mitsuru
N1 - Funding Information:
This work was supported by the Sumitomo Foundation and Grants-in-Aid for Scientific Research from the Ministry of Education, Culture, Sports, Science and Technology of Japan. The authors thank Drs H. Osada and H. Kakeya, of RIKEN, for sending us NMR data for NG-391 and for helpful discussion throughout the course of this research. The authors are grateful to Shinetsu-Kagaku Corporation for the gift of TBSCl.
PY - 2002/12/2
Y1 - 2002/12/2
N2 - The stereocontrolled total synthesis of (+)-NG-391, a neuronal cell-protecting molecule, is described along with the determination of its absolute stereochemistry. The following reactions in this synthesis are particularly noteworthy: (1) The stereoselective construction of the conjugated (E,E,E,E,E)-pentaene from an (E,E,E)-alcohol using an IBX oxidation followed by stereoselective Horner-Emmons reaction. (2) The (E)-selective Knoevenagel condensation of a β-ketonitrile with a chiral 2-alkoxyaldehyde prepared from (S)-malic acid. (3) A diastereoselective epoxidation.
AB - The stereocontrolled total synthesis of (+)-NG-391, a neuronal cell-protecting molecule, is described along with the determination of its absolute stereochemistry. The following reactions in this synthesis are particularly noteworthy: (1) The stereoselective construction of the conjugated (E,E,E,E,E)-pentaene from an (E,E,E)-alcohol using an IBX oxidation followed by stereoselective Horner-Emmons reaction. (2) The (E)-selective Knoevenagel condensation of a β-ketonitrile with a chiral 2-alkoxyaldehyde prepared from (S)-malic acid. (3) A diastereoselective epoxidation.
KW - IBX oxidation
KW - Knoevenagel reaction
KW - NG-391
KW - Natural product
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U2 - 10.1016/S0040-4020(02)01290-5
DO - 10.1016/S0040-4020(02)01290-5
M3 - Article
AN - SCOPUS:0037010766
SN - 0040-4020
VL - 58
SP - 9839
EP - 9846
JO - Tetrahedron
JF - Tetrahedron
IS - 49
ER -