jo201005d_si_001.pdf (4.62 MB)
A Chemoenzymatic Total Synthesis of (+)-Clividine
journal contribution
posted on 2011-08-05, 00:00 authored by Lorenzo
V. White, Brett D. Schwartz, Martin G. Banwell, Anthony C. WillisThe 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.