Short Synthesis of Berkeleyamide D and Determination of the Absolute Configuration by the Vibrational Circular Dichroism Exciton Chirality Method
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- 作者：Kenta Komori ; Tohru Taniguchi ; Shoma Mizutani ; Kenji Monde ; Kouji Kuramochi ; Kazunori Tsubaki
- 刊名：Organic Letters
- 出版年：2014
- 出版时间：March 7, 2014
- 年：2014
- 卷：16
- 期：5
- 页码：1386-1389
- 全文大小：315K
- 年卷期：v.16,no.5(March 7, 2014)
- ISSN：1523-7052
文摘
The first synthesis of (卤)-berkeleyamide D has been accomplished. The key features of this synthesis include the formation of an 伪,尾-epoxy-纬-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.