Synthesis of the pyrrolidinone core of KSM-2690 B.
[reaction: see text] The first synthesis of the pyrrolidinone core of the polyene beta-lactone antibiotic KSM-2690 B is described. An ammonia-free Birch reductive aldol reaction utilizing acetaldehyde is one of the key steps, together with a ruthenium-catalyzed alkene isomerization reaction.
Donohoe
Timothy J
TJ
Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford OX1 3TA, U.K. timothy.donohoe@chem.ox.ac.uk
Chiu
Jessica Y K
JY
Thomas
Rhian E
RE
D000079:Acetaldehyde / Q000737:chemistry; D000475:Alkenes / Q000737:chemistry; D000641:Ammonia / Q000737:chemistry; D000900:Anti-Bacterial Agents / Q000737:chemistry*; D002384:Catalysis; D007536:Isomerism; D007783:Lactones / Q000737:chemistry*; D008956:Models, Chemical; D010080:Oxazoles / Q000737:chemistry*; D010084:Oxidation-Reduction; D011760:Pyrrolidinones / Q000138:chemical synthesis*; D012238:Rhodium / Q000737:chemistry; D013141:Spiro Compounds / Q000737:chemistry*
D000475:Alkenes; D000900:Anti-Bacterial Agents; D007783:Lactones; D010080:Oxazoles; D011760:Pyrrolidinones; D013141:Spiro Compounds; C077919:diffusomycin; D000641:Ammonia; D012238:Rhodium; D000079:Acetaldehyde