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Synthesis 2010(16): 2799-2803
DOI: 10.1055/s-0030-1258143
DOI: 10.1055/s-0030-1258143
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New YorkCarbohydrate-Derived Bis(oxazoline) Ligand in the Total Synthesis of Grenadamide
Further Information
Received
10 March 2010
Publication Date:
01 July 2010 (online)
Publication History
Publication Date:
01 July 2010 (online)
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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