Enantioselective synthesis of the pyrroloquinoline core of the martinellines.
[equation--see text] The first enantioselective synthesis of the martinelline core (-)-3 is reported. The synthesis of (-)-3 from N-allyl-N-(benzyloxycarbonyl)-2-iodoaniline (12) proceeded in seven steps and 23% overall yield. In addition, the preparation of a carbocyclic model system is described.
Nieman
J A
JA
Structural, Analytical & Medicinal Chemistry, Pharmacia & Upjohn, Inc., Kalamazoo, MI 49001, USA.
Ennis
M D
MD
D018360:Crystallography, X-Ray; D007202:Indicators and Reagents; D008958:Models, Molecular; D015394:Molecular Structure; D010946:Plants, Medicinal; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry*; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
D007202:Indicators and Reagents; D011758:Pyrroles; D011804:Quinolines; C410408:martinelline; C410406:pyrroloquinoline