ol6b03550_si_001.pdf (5.97 MB)
Asymmetric Total Synthesis of Lepadiformine C Using Memory of Chirality in an Intramolecular Ester Enolate Michael Addition
journal contribution
posted on 2016-12-21, 13:33 authored by Seokwoo Lee, Minsik Bae, Jinkyung In, Jae Hyun Kim, Sanghee KimThe asymmetric synthesis
of lepadiformine C was achieved using d-proline as the only
chiral source. The synthetic strategy
features the use of the principle of “memory of chirality”
in an intramolecular Michael addition to construct the bicyclic intermediate
without the aid of external chiral sources. A brief mechanistic rationale
is presented to account for the stereochemical outcome.