Synthesis of the C-13 side chain precursors of the 9-dihydrotaxane analogue ABT-271

M R Leanna; J A DeMattei; W Li; P J Nichols; M Rasmussen; H E Morton

doi:10.1021/ol006508o

Synthesis of the C-13 side chain precursors of the 9-dihydrotaxane analogue ABT-271

Org Lett. 2000 Nov 16;2(23):3627-30. doi: 10.1021/ol006508o.

Authors

M R Leanna¹, J A DeMattei, W Li, P J Nichols, M Rasmussen, H E Morton

Affiliation

¹ Process Chemistry, D-45L/R8, Pharmaceutical Products Division, Abbott Laboratories, 1401 Sheridan Road, North Chicago, Illinois 60064-6285, USA.

PMID: 11073661
DOI: 10.1021/ol006508o

Abstract

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.

MeSH terms

Antineoplastic Agents, Phytogenic / chemical synthesis*
Antineoplastic Agents, Phytogenic / chemistry
Chromatography, High Pressure Liquid
Indicators and Reagents
Magnetic Resonance Spectroscopy
Paclitaxel / analogs & derivatives*
Paclitaxel / chemical synthesis*
Paclitaxel / chemistry
Plants, Medicinal / chemistry*
Stereoisomerism

Substances

Antineoplastic Agents, Phytogenic
Indicators and Reagents
Paclitaxel