Explorations on the asymmetric total synthesis of isoschizogamine.
Two approaches to the synthesis of isoschizogamine were reported. Both routes utilized an efficient aza-Claisen rearrangement to establish the absolute stereochemistry of the all-carbon quaternary center in the natural product. In the first approach, a highly diastereoselective (10:1) hetero-Diels-Alder reaction was utilized to reach a densely functionalized tetrahydroquinoline derivative as an advanced intermediate to the targeted alkaloid. An acylamidine intermediate was prepared and studied in the intramolecular cyclization reaction under acidic conditions in our second approach.
Zhou
Jianguang
J
Department of Chemistry, University of Rochester, Rochester, New York 14627, USA. jzhou@mail.chem.tamu.edu
Magomedov
Nabi A
NA