Concise synthesis of the bacterial DNA primase inhibitor (+) -Sch 642305.
[structure: see text]. A highly convergent, enantioselective synthesis of (+) -Sch 642305 is presented, which features a Mukaiyama-Michael addition followed by allylation to establish the syn-anti relationship of the three contiguous stereocenters. The 10-membered macrolactone was formed through ring-closing metathesis.
Wilson
Erica M
EM
Department of Chemistry, University of California, Berkeley, CA 94720, USA.
Trauner
Dirk
D
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D003512:Cyclohexanones / Q000737:chemistry; D053138:Cyclohexenes / Q000737:chemistry; D019915:DNA Primase / Q000037:antagonists & inhibitors*; D004269:DNA, Bacterial / Q000187:drug effects*; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D015394:Molecular Structure; D013237:Stereoisomerism
D000900:Anti-Bacterial Agents; D003512:Cyclohexanones; D053138:Cyclohexenes; D004269:DNA, Bacterial; D004791:Enzyme Inhibitors; D018942:Macrolides; C482741:Sch 642305; D019915:DNA Primase