Formal total synthesis of platencin.
The right bicycle: A concise formal synthesis of platencin was based on an efficient oxygen-mediated palladium-catalyzed cycloalkenylation of 1 to form a bicyclo[3.2.1]octane, and a deoxygenative rearrangement of tosylhydrazone 2 to construct the bicyclo[2.2.2]octane 3. The total yield of the core structure 4 of platencin was 17.5% for 13 steps from a commercially available compound. Ts = p-toluenesulfonyl, TBS = tert-butyldimethylsilyl, Piv = pivaloyl.
Institut für Organische Chemie, Universität Tübingen, Auf der Morgenstelle 18, 72076 Tübingen, Germany.
Georgy N
GN
Varseev
Martin E
ME
Maier
D000627:Aminophenols / Q000138:chemical synthesis*; D002384:Catalysis; D010165:Palladium / Q000737:chemistry*; D011083:Polycyclic Compounds / Q000138:chemical synthesis*
D000627:Aminophenols; D011083:Polycyclic Compounds; D010165:Palladium; C520340:platencin