Krishnadimer A, an Axially Chiral Non-biaryl Natural Product: Discovery and Biomimetic Synthesis
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- 作者：Wan Shan Li ; Jun Wu ; Jun Li ; Tirumani Satyanandamurty ; Li ShenGerhard Bringmann
- 刊名：Organic Letters
- 出版年：2017
- 出版时间：January 6, 2017
- 年：2017
- 卷：19
- 期：1
- 页码：182-185
- 全文大小：389K
- ISSN：1523-7052
文摘
Krishnadimer A (1a), a C2-symmetric limonoid dimer representing a new class of axially chiral nonbiaryl natural products, was isolated and biomimetically semisynthesized by atroposelective 2,3-dichloro-5,6-dicyanobenzoquinone-mediated dienol-oxidative coupling. Single-crystal X-ray diffraction and electronic circular dichroism spectral analysis on the synthesized 1a unambiguously established its absolute configuration, including the P-configuration of the C15–C15′ central axis. Antitumor investigations of the synthesized dimers 1a, 2a, and 2b revealed the large impact of axial chirality on bioactivities.