Synthesis of Phoslactomycin I-i
Yuichi Kobayashi1, Mohammad Nuruzzaman1, Narihito Ogawa1
1Department of Bioengineering, Tokyo Institute of Technology, Midori-ku, Yokohama 226-8501, Japan.
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.
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