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Synfacts 2011(2): 0126-0126  
DOI: 10.1055/s-0030-1259220
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Lactimidomycin

Contributor(s): Steven V. Ley, Kimberley A. Roper
K. Micoine, A. Fürstner*
Max-Planck-Institut für Kohlenforschung, Mülheim/Ruhr, Germany
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Publikationsdatum:
19. Januar 2011 (online)

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Significance

Lactimidomycin is an antiproliferative macrolide and cell migration inhibitor with a strained twelve-membered 1,3-diene ring. This first synthesis consists of a counterintuitive temporary increase of ring strain using an alkyne ring-closing metathesis to give the Z-enyne H, before reducing this regioselectively and appending the side chain stereoselectively using a Mukaiyama ­aldol reaction.