A concise total synthesis of (+/-)-1-epiaustraline.
[reaction: see text] A concise total synthesis of 1-epiaustraline 3 is described that utilizes a diastereoselective Birch reduction of an electron-deficient pyrrole and a chelation-controlled vinyl Grignard addition to an aldehyde to introduce the C7 stereocenter. The C1 and C2 stereocenters were set through an OsO(4)-catalyzed dihydroxylation.
Donohoe
Timothy J
TJ
Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford OX1 3TA, UK. timothy.donohue@chem.ox.ac.uk
Sintim
Herman O
HO
D002384:Catalysis; D008968:Molecular Conformation; D009993:Osmium Tetroxide / Q000737:chemistry; D011763:Pyrrolizidine Alkaloids / Q000138:chemical synthesis*; D013237:Stereoisomerism
D011763:Pyrrolizidine Alkaloids; C412020:epiaustraline; D009993:Osmium Tetroxide