Enantioselective modular synthesis of cyclohexenones: total syntheses of (+)-crypto- and (+)-infectocaryone.
A modular synthesis of cyclohexenones is described and applied to the first enantioselective total syntheses of (+)-crypto- and (+)-infectocaryone. Key steps in the synthesis of cyclohexenones are an iridium-catalyzed allylic alkylation, nucleophilic allylation, and ring-closing metathesis. On the way to (+)-cryptocaryone, a catch and release strategy involving an iodolactonization/elimination and a regioselective C-acylation were used.
Franck
Géraldine
G
Organisch-Chemisches Institut der Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, D-69120 Heidelberg, Germany.
Brödner
Kerstin
K
Helmchen
Günter
G
D000215:Acylation; D000478:Alkylation; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D003500:Cyclization; D003512:Cyclohexanones / Q000138:chemical synthesis* / Q000737:chemistry; D007495:Iridium / Q000737:chemistry*; D015394:Molecular Structure; D011753:Pyrones / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D003512:Cyclohexanones; D011753:Pyrones; C548572:cryptocaryone; C553701:infectocaryone; D007495:Iridium