Synthesis of Phoslactomycin I-i.

Abstract

The C5-C11 moiety of phoslactomycin I-i was synthesized via chelation-controlled addition of CH₂═CHMgBr to the C8 ketone, ozonolysis, and the HWE reaction. The TMS acetylene and C1-C4 were attached to C11 and C5, respectively. A cyclohexyl moiety possessing an iodovinyl group was synthesized from quinic acid. The coupling reaction of the intermediates followed by Zn reduction yielded the cis,cis-diene. Finally, the amino and phosphate groups were attached.