Synthesis of the C-13 side chain precursors of the 9-dihydrotaxane analogue ABT-271.
N-Boc-L-Leucinol was converted to two C-13 side chain precursors of the 9-dihydrotaxane analogue ABT-271. The trans-oxazolidine acid 4 and the cis-Boc-lactam 2b were prepared in 44% and 40% overall yield, respectively, and with excellent (>98%) stereochemical purity.
Leanna
M R
MR
Process Chemistry, D-45L/R8, Pharmaceutical Products Division, Abbott Laboratories, 1401 Sheridan Road, North Chicago, Illinois 60064-6285, USA.
DeMattei
J A
JA
Li
W
W
Nichols
P J
PJ
Rasmussen
M
M
Morton
H E
HE
D000972:Antineoplastic Agents, Phytogenic / Q000138:chemical synthesis* / Q000737:chemistry; D002851:Chromatography, High Pressure Liquid; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D017239:Paclitaxel / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D010946:Plants, Medicinal / Q000737:chemistry*; D013237:Stereoisomerism
D000972:Antineoplastic Agents, Phytogenic; D007202:Indicators and Reagents; D017239:Paclitaxel