Enantioselective synthesis of (-)-platensimycin oxatetracyclic core by using an intramolecular Diels-Alder reaction.
An enantioselective route to the oxatetracyclic core of (-)-platensimycin (1) has been investigated by using an intramolecular Diels-Alder reaction as the key step. The thermal reaction of E/Z mixture (1:1) provided oxatetracyclic core 2 from the E-diene and the Z-diene was recovered unchanged. The Diels-Alder substrate was conveniently assembled in optically active form with use of (S)-carvone as the starting material.
Ghosh
Arun K
AK
Department of Chemistry, Purdue University, West Lafayette, Indiana 47907, USA. akghosh@purdue.edu
Xi
Kai
K
D000218:Adamantane / Q000138:chemical synthesis* / Q000737:chemistry; D062365:Aminobenzoates / Q000138:chemical synthesis* / Q000737:chemistry; D000813:Anilides / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D007659:Ketones / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D015394:Molecular Structure; D013237:Stereoisomerism
D062365:Aminobenzoates; D000813:Anilides; D007659:Ketones; D000218:Adamantane; C510909:platensimycin