Cycloaddition reactions of imines with 3-thiosuccinic anhydrides: synthesis of the tricyclic core of martinellic acid.
Arylthio-substituted succinic anhydrides undergo cycloaddition reactions with imines to produce gamma-lactams in high yield and with high diastereoselectivity. The origin of the selectivity is proposed to result from anion-pi repulsion in the transition state. The utility of this technique is demonstrated in a synthesis of the carbon framework common to the alkaloids martinellic acid and martinelline in five steps.
Ng
Pui Yee
PY
Broad Institute of Harvard and MIT, Chemical Biology Program, 7 Cambridge Center, Cambridge, MA 02142, USA.
Masse
Craig E
CE
Shaw
Jared T
JT
D000812:Anhydrides / Q000737:chemistry*; D007097:Imines / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D011758:Pyrroles / Q000138:chemical synthesis*; D011804:Quinolines / Q000138:chemical synthesis*
D000812:Anhydrides; D007097:Imines; D011758:Pyrroles; D011804:Quinolines; C432345:martinellic acid