ol500148g_si_001.pdf (3.12 MB)
Short Synthesis of Berkeleyamide D and Determination of the Absolute Configuration by the Vibrational Circular Dichroism Exciton Chirality Method
journal contribution
posted on 2014-03-07, 00:00 authored by Kenta Komori, Tohru Taniguchi, Shoma Mizutani, Kenji Monde, Kouji Kuramochi, Kazunori TsubakiThe
first synthesis of (±)-berkeleyamide D has been accomplished.
The key features of this synthesis include the formation of an α,β-epoxy-γ-lactam
via a Darzens reaction and the construction of a spirocyclic ring
system by a C-acylation reaction followed by an intramolecular
spirocyclization via an epoxide-opening reaction. Following optical
resolution by chiral HPLC, the absolute configurations of both enantiomers
of berkeleyamide D were determined by the vibrational circular dichroism
exciton chirality method.