title: Short synthesis of berkeleyamide D and determination of the absolute configuration by the vibrational circular dichroism exciton chirality method.
abstract: The 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.
authors: Graduate School for Life and Environmental Sciences, Kyoto Prefectural University , 1-5 Shimogamo Hangi-cho, Sakyo-ku, Kyoto 606-8522, Japan.
authors: Kenta
authors: K
authors: Komori
authors: Tohru
authors: T
authors: Taniguchi
authors: Shoma
authors: S
authors: Mizutani
authors: Kenji
authors: K
authors: Monde
authors: Kouji
authors: K
authors: Kuramochi
authors: Kazunori
authors: K
authors: Tsubaki
mesh_terms: D002942:Circular Dichroism; D007769:Lactams / Q000138:chemical synthesis*; D015394:Molecular Structure; D010407:Penicillium / Q000737:chemistry; D011760:Pyrrolidinones / Q000737:chemistry / Q000302:isolation & purification*; D013237:Stereoisomerism
chemical_list: D007769:Lactams; D011760:Pyrrolidinones; C000588722:berkeleyamide D