Synthesis of PhoslactomycinI‑i

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 <i>cis</i>,<i>cis</i>-diene. Finally, the amino and phosphate groups were attached.