TY - JOUR
T1 - Total synthesis of actinobolin from d-glucose by way of the stereoselective three-component coupling reaction
AU - Imuta, Satoshi
AU - Tanimoto, Hiroki
AU - Momose, Miho K.
AU - Chida, Noritaka
N1 - Funding Information:
We thank Dr. Y. Nishimura (Institute of Microbial Chemistry, Tokyo, Japan) for a generous gift of natural actinobolin. We also thank the Ministry of Education, Culture, Sports, Science, and Technology, Japan (Grant-in-Aid for Scientific Research, B15350027 and Grant-in-Aid for the 21st Century COE program ‘KEIO LCC’) for financial assistance.
PY - 2006/7/17
Y1 - 2006/7/17
N2 - The total synthesis of (-)-actinobolin 3, an antipode of the natural product, starting from d-glucose is described. A three-component coupling reaction of functionalized cyclohexenone (+)-6 derived from d-glucose by way of Ferrier's carbocyclization reaction, with vinyl cuprate and 2-alkoxypropanal 7 effectively constructed the carbon framework of 3 in a highly stereoselective manner. In an aldol process of the three-component coupling reaction, stereochemical control (chelation and Felkin-Anh conditions) was achieved by the choice of the protecting groups of a hydroxy function in 2-hydroxypropanal and the reaction solvents. The formal synthesis of the natural enantiomer, (+)-actinobolin 1, starting from d-glucose was also accomplished.
AB - The total synthesis of (-)-actinobolin 3, an antipode of the natural product, starting from d-glucose is described. A three-component coupling reaction of functionalized cyclohexenone (+)-6 derived from d-glucose by way of Ferrier's carbocyclization reaction, with vinyl cuprate and 2-alkoxypropanal 7 effectively constructed the carbon framework of 3 in a highly stereoselective manner. In an aldol process of the three-component coupling reaction, stereochemical control (chelation and Felkin-Anh conditions) was achieved by the choice of the protecting groups of a hydroxy function in 2-hydroxypropanal and the reaction solvents. The formal synthesis of the natural enantiomer, (+)-actinobolin 1, starting from d-glucose was also accomplished.
KW - Actinobolin
KW - Ferrier's carbocyclization
KW - Three-component coupling reaction
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U2 - 10.1016/j.tet.2006.04.079
DO - 10.1016/j.tet.2006.04.079
M3 - Article
AN - SCOPUS:33744903685
SN - 0040-4020
VL - 62
SP - 6926
EP - 6944
JO - Tetrahedron
JF - Tetrahedron
IS - 29
ER -