Asymmetric syntheses of (+)-negamycin, (+)-3-epi-negamycin and sperabillin C (cas 111337-84-9) via lithium amide conjugate addition

Add time:08/29/2019    Source:sciencedirect.com

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 (cas 111337-84-9) (in 17 steps and 13% overall yield) from commercially available starting materials.

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