Crotylboron-based synthesis of the polypropionate units of chaxamycins A/D, salinisporamycin, and rifamycin S.
Syntheses of the C(15)-C(27) fragments of chaxamycins A/D, rifamycin S, and the C(12)-C(24) fragment of salinisporamycin have been accomplished in 10 steps from commercially available starting materials. Three crotylboron reagents were utilized to construct the seven contiguous stereocenters in these fragments with excellent stereoselectivity.
Department of Chemistry, The Scripps Research Institute, Scripps Florida, Jupiter, Florida 33458, United States.
Ming
M
Chen
William R
WR
Roush
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry; D007202:Indicators and Reagents / Q000737:chemistry; D012294:Rifamycins / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000900:Anti-Bacterial Agents; D007202:Indicators and Reagents; D012294:Rifamycins; C581434:chaxamycin A; C581435:chaxamycin D; C544882:salinisporamycin; C032779:rifamycin S