Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 72, Issue 8, Pages 2744-2756Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo062089i
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The total synthesis of borrelidin has been achieved. The best feature of our synthetic route is macrocyclization at C11-C12 for the construction of an 18-membered ring after esterification between two segments. A detailed examination of the macrocyclization led us to the samarium(II) iodide-mediated intramolecular Reformatsky-type reaction as the most efficient synthetic approach. The two key segments were synthesized through regioselective methylation, directed hydrogenation, stereoselective Reformatsky-type reaction, and MgBr2 center dot Et2O-mediated chelation-controlled allylation.
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