Diastereoselective synthesis of pyrrolidines using a nitrone/cyclopropane cycloaddition: synthesis of the tetracyclic core of nakadomarin A.
The synthesis of the tetracyclic core of nakadomarin A is described. The core contains all the heterocycles and the required stereocenters found in the natural product and provides a promising route to the target itself. The strategy utilizes a general, diastereoselective pyrrolidine synthesis that proceeds via a homo 3 + 2 dipolar cycloaddition. The scope of this methodology is also described. [structure: see text]
Young
Ian S
IS
Department of Chemistry, The University of Western Ontario, London, Ontario, Canada N6A 5B7.
Williams
Justin L
JL
Kerr
Michael A
MA
D002243:Carbolines / Q000138:chemical synthesis*; D002384:Catalysis; D003500:Cyclization; D003521:Cyclopropanes / Q000737:chemistry; D015394:Molecular Structure; D009589:Nitrogen Oxides / Q000737:chemistry; D011759:Pyrrolidines / Q000138:chemical synthesis*; D013237:Stereoisomerism
D002243:Carbolines; D003521:Cyclopropanes; D009589:Nitrogen Oxides; D011759:Pyrrolidines; C476640:nakadomarin A; C015388:nitrones; C030797:cyclopropane