Supporting Information
© Wiley-VCH 2006
69451 Weinheim, Germany
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Supporting Information
Formal Synthesis of (+)-Catharanthine
Lionel Moisan, Pierre Thuéry, Marc Nicolas, Eric Doris,* and Bernard Rousseau
General procedures. Unless otherwise specified, chemicals were purchased from
Aldrich co. and used without further purification. Reactions were carried out under
nitrogen using dry solvent, unless otherwise noted. THF, Et2O and CH2Cl2 were distilled
respectively from sodium/benzophenone ketyl and calcium hydride before use. Flash
chromatography was carried out on Kieselgel 60 (230-240 mesh, Merck) and analytical
TLC was performed on Merck precoated silica gel (60 F254); visualization was carried out
with UV and/or heating with a solution of 5-7% phosphomolybdic acid in ethanol.
Melting points were determined using open-ended capillary tubes on a Büchi 535
apparatus and are uncorrected. Microanalyses were performed at the “Service de
Microanalyse de l’Institut des Substances Naturelles” in Gif-sur-Yvette (France). Mass
spectra were recorded on an ESI-TOF Mariner spectrometer. HRMS were recorded at the
“Service de Spectrometrie de Masse de l’Institut des Substances Naturelles” in Gif-sur-
Yvette (France). 1H and 13C spectra were recorded either on a Bruker AC 300
spectrometer at 300.13 and 75.47 MHz or a Bruker AVANCE DPX 400 spectrometer at
400.13 and 100.61 MHz. Unless otherwise specified, spectra were recorded in CDCl3;
chemical shifts (δ) are expressed in ppm and coupling constant (J) in Hertz. IR spectra
were recorded on a Perkin-Elmer System 2000 FT-IR. Optical rotations were determined
using the sodium D line (589 nm) on a Perkin Elmer 341 polarimeter.
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(S)-2-Oxo-oxazolidine-4-carboxylic acid (6)
NH
O
O
OH
O
At 0°C, to (L)-carbobenzyloxyserine (25.34 g, 106 mmol, 1 equiv) is added a NaOH
solution (8.0 g, 1.9 equiv) in 40 mL of H2O. The solid quickly dissolves and the solution
is stirred at rt for 30 min. The mixture is then washed with Et