Novel synthesis of 2-substituted 19-norvitamin D A-ring phosphine oxide from D-glucose as a building block.
19-norvitamin D A-ring phosphine oxide 5 was synthesized by a new sequence mode starting from D-glucose as a chiral template. Transformation of the pyranoside ring into the A-ring carbocycle was achieved by the Pd-catalyzed Ferrier rearrangement. The phosphine oxide 5 was obtained in an 18% overall yield by this novel cost-effective method.
Shimizu
Masato
M
Institute of Biomaterials and Bioengineering, Tokyo Medical and Dental University, 2-3-10 Kandasurugadai, Chiyoda-ku, Tokyo 101-0062, Japan. shimizu.mr@tmd.ac.jp
Iwasaki
Yukiko
Y
Shibamoto
Yoshinori
Y
Sato
Miki
M
DeLuca
H F
HF
Yamada
Sachiko
S
D002117:Calcitriol / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D002384:Catalysis; D005947:Glucose / Q000737:chemistry*; D010087:Oxides / Q000138:chemical synthesis* / Q000737:chemistry; D010165:Palladium / Q000737:chemistry; D010720:Phosphines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D010087:Oxides; D010720:Phosphines; D010165:Palladium; D002117:Calcitriol; D005947:Glucose