Diastereoselective formal total synthesis of the DNA polymerase alpha inhibitor, aphidicolin, using palladium-catalyzed cycloalkenylation and intramolecular Diels-Alder reactions.
[structure: see text] A novel diastereoselective formal synthesis of aphidicolin has been achieved by exploiting a unique characteristic of a bicyclo[3.2.1]octane prepared by employing a palladium-catalyzed cycloalkenylation process.
Toyota
Masahiro
M
Department of Organic Chemistry, Graduate School of Pharmaceutical Science, Tohoku University, Aobayama, Sendai 980-8578, Japan. mihara@mail.pharm.tohoku.ac.jp
Sasaki
Masato
M
Ihara
Masataka
M
D016590:Aphidicolin / Q000138:chemical synthesis* / Q000494:pharmacology; D002384:Catalysis; D003500:Cyclization; D004256:DNA Polymerase I / Q000037:antagonists & inhibitors*; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000494:pharmacology; D009795:Octanes / Q000737:chemistry; D009942:Organometallic Compounds / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism
D004791:Enzyme Inhibitors; D009795:Octanes; D009942:Organometallic Compounds; D016590:Aphidicolin; D010165:Palladium; D004256:DNA Polymerase I; C026728:octane