Studies on the total synthesis of formamicin: synthesis of the C(1)-C(11) fragment.
[figure: see text] An efficient and highly concise synthesis of 6, corresponding to the C(1)-C(11) fragment of formamicin (1), has been accomplished by a route utilizing a diastereoselective lactate aldol reaction to set the C(6) tertiary ether and the TES-OTf mediated transketalization of the C(6) tertiary methoxymethyl ether and the C(25) PMB ether to set the seven-membered methylene acetal unit (see 37-->38).
Powell
N A
NA
Department of Chemistry, University of Michigan, 930 North University, Ann Arbor, Michigan 48109, USA.
Roush
W R
WR
D000192:Actinomycetales / Q000737:chemistry; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis*; D000935:Antifungal Agents / Q000138:chemical synthesis*; D018942:Macrolides
D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; D018942:Macrolides; C111293:formamicin