A Chemoenzymatic Total Synthesis of (+)-Clividine

作者：White Lorenzo V; Schwartz Brett D; Banwell Martin G^*; Willis Anthony C

来源：Journal of Organic Chemistry, 2011, 76(15): 6250-6257.

DOI：10.1021/jo201005d

The title compound, ent-1, the non-natural enantiomeric form of the lycorenine-type alkaloid (-)-clividine (1), has been prepared using the enantiomerically pure (ee >99.8%) cis-1,2-dihydrocatechol 3 as starting material. A key feature associated with the closing stages of the synthesis involved the diastereoselective addition of a nitrogen-centered radical onto a pendant cyclohexene to establish the cis-fused D-ring and the required stereochemistry at C11b in the final product ent-1.

• 出版日期2011-8-5