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Synthesis 2010(16): 2799-2803  
DOI: 10.1055/s-0030-1258143
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Carbohydrate-Derived Bis(oxazoline) Ligand in the Total Synthesis of Grenadamide

Tobias Minuth, Mike M. K. Boysen*
Institute of Organic Chemistry, Gottfried Wilhelm Leibniz University of Hannover, Schneiderberg 1B, 30167 Hannover, Germany
Fax: +49(511)7623011; e-Mail: mike.boysen@oci.uni-hannover.de;
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Publikationsverlauf

Received 10 March 2010
Publikationsdatum:
01. Juli 2010 (online)

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Abstract

Using an optimised carbohydrate-based bis(oxazoline) ligand and copper(I) triflate, unactivated aliphatic alkenes were cyclopropanated­ with simple ethyl diazoacetate, giving the corresponding products in good yields and high stereoselectivities. The trans-disubstituted cyclopropyl carboxylic acid ester derived from 1-nonene was subsequently used as the key intermediate for the synthesis of the (+)-enantiomer of the natural product (-)-grenadamide. The efficient and high-yielding approach towards grenadamide reported here is the first to utilise asymmetric cyclopropanation for the construction of the chiral cyclopropyl unit.

Key words

carbohydrates - ligand design - asymmetric catalysis - natural products - cyclopropanation

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