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The chemo- and enantioselective reduction of ethyl 4-chloroacetoacetate and the diastereoselective conjugate addition of enantiopure lithium N-benzyl-N-(α-methylbenzyl)amide to an α,β-unsaturated ester have been used as the key steps in the total asymmetric syntheses of (+)-negamycin (in 13 steps and 24% overall yield), (+)-3-epi-negamycin (in 13 steps and 10% overall yield) and sperabillin C (in 17 steps and 13% overall yield) from commercially available starting materials. © 2010 Elsevier Ltd. All rights reserved.

Original publication

DOI

10.1016/j.tet.2010.10.067

Type

Journal article

Journal

Tetrahedron

Publication Date

07/01/2011

Volume

67

Pages

216 - 227