TY - JOUR
T1 - Intramolecular aldol condensation applied to d-glucose-derived δ-ketoaldehydes
T2 - access to enantiomerically pure six-membered carbocycles
AU - Tadano, Kin ichi
AU - Kanazawa, Satoshi
AU - Takao, Ken ichi
AU - Ogawa, Seiichiro
PY - 1992
Y1 - 1992
N2 - An enantiomerically pure δ-ketoaldehyde 10, efficiently prepared from D-glucose, was subjected to an intramolecular aldol condensation. By using DBU as a base, the expecting aldol reaction took place smoothly giving the aldol 11 stereoselectively. Further functionalization of 11 provided tri-C-substituted cyclohexanediols 26 and 27, via the functionalized cyclohexenone15.
AB - An enantiomerically pure δ-ketoaldehyde 10, efficiently prepared from D-glucose, was subjected to an intramolecular aldol condensation. By using DBU as a base, the expecting aldol reaction took place smoothly giving the aldol 11 stereoselectively. Further functionalization of 11 provided tri-C-substituted cyclohexanediols 26 and 27, via the functionalized cyclohexenone15.
KW - D-glucose-derived δ-ketoaldehyde
KW - intramolecular aldol condensation
KW - tri-C-alkylated cyclohexanoids
UR - http://www.scopus.com/inward/record.url?scp=0026697107&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0026697107&partnerID=8YFLogxK
U2 - 10.1016/S0040-4020(01)80440-3
DO - 10.1016/S0040-4020(01)80440-3
M3 - Article
AN - SCOPUS:0026697107
SN - 0040-4020
VL - 48
SP - 4283
EP - 4300
JO - Tetrahedron
JF - Tetrahedron
IS - 21
ER -