Studies in macrolide antibiotic synthesis: the role of tethered alkoxides in titanium alkoxide-mediated regioselective reductive coupling reactions.
[reaction: see text] A convergent route to a C1-C15 fragment precursor for erythromycin-based macrolide antibiotics is presented. These studies define a role for tethered alkoxides in the control of site-selective carbon-carbon bond formation in titanium alkoxide-mediated coupling reactions of internal alkynes and chiral aldehydes.
Bahadoor
Adilah B
AB
Department of Chemistry, Yale University, New Haven, Connecticut 06520-8107, USA.
Micalizio
Glenn C
GC
D000438:Alcohols / Q000737:chemistry; D000480:Alkynes / Q000138:chemical synthesis / Q000737:chemistry; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry*; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry*; D010087:Oxides / Q000737:chemistry; D013237:Stereoisomerism; D013302:Streptomyces / Q000737:chemistry; D014025:Titanium / Q000737:chemistry*
D000438:Alcohols; D000480:Alkynes; D000900:Anti-Bacterial Agents; D018942:Macrolides; D010087:Oxides; D014025:Titanium