Complementary chemoenzymatic routes to both enantiomers of febrifugine

Marloes A. Wijdeven; Rutger J. F. van den Berg; Roel Wijtmans; Peter N. M. Botman; Richard H. Blaauw; Hans E. Schoemaker; Floris L. van Delft; Floris P. J. T. Rutjes

doi:10.1039/B901670H

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Organic & Biomolecular Chemistry

Issue 14, 2009

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Complementary chemoenzymatic routes to both enantiomers of febrifugine

Marloes A. Wijdeven , Rutger J. F. van den Berg , Roel Wijtmans , Peter N. M. Botman , Richard H. Blaauw , Hans E. Schoemaker , Floris L. van Delft and Floris P. J. T. Rutjes

Org. Biomol. Chem., 2009, 7, 2976-2980

DOI: 10.1039/B901670H
Received 26 Jan 2009, Accepted 30 Apr 2009
First published on the web 04 Jun 2009

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Two complementary strategies for the synthesis of febrifugine are detailed based on previously developed chemoenzymatic approaches to the 3-hydroxypiperidine skeleton. The introduction of the quinazolone-containing side chain in both strategies was based on an N-acyliminium ion-mediated coupling reaction.

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Experimental procedures of compounds 4, 16–20, 22 and ¹H and ¹³C spectra of all new compounds
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Articles By

Marloes A. Wijdeven
Rutger J. F. van den Berg
Roel Wijtmans
Peter N. M. Botman
Richard H. Blaauw
Hans E. Schoemaker
Floris L. van Delft
Floris P. J. T. Rutjes

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Organic & Biomolecular Chemistry

Complementary chemoenzymatic routes to both enantiomers of febrifugine

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