A total synthesis of tarchonanthuslactone exploiting N-pyrrole carbinols as efficient stereocontrolling elements.
[reaction: see text] A short stereoselective total synthesis of the polyketide natural product, tarchonanthuslactone, has been achieved. The key sequence involves the first reported catalytic enantioselective reduction of an N-acyl pyrrole and subsequent use of this stereocenter in a diastereoselective reductive cascade. This proceeded with unprecedentedly high stereocontrol and offered an elegant method of generating the desired syn stereochemistry present in the final target in one step.
Scott
Mark S
MS
University Chemical Laboratory, University of Cambridge, Lensfield Road, Cambridge, CB2 1EW, United Kingdom.
Luckhurst
Chris A
CA
Dixon
Darren J
DJ
D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D000432:Methanol / Q000031:analogs & derivatives* / Q000737:chemistry*; D015394:Molecular Structure; D011753:Pyrones / Q000138:chemical synthesis* / Q000737:chemistry; D011758:Pyrroles / Q000737:chemistry*; D013237:Stereoisomerism
D001688:Biological Products; D011753:Pyrones; D011758:Pyrroles; C427965:tarchonanthuslactone; D000432:Methanol