Krishnadimer A, an Axially Chiral Non-biaryl Natural Product: Discovery and Biomimetic Synthesis
- 19 December 2016
- journal article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 19 (1), 182-185
- https://doi.org/10.1021/acs.orglett.6b03479
Abstract
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.Keywords
Funding Information
- Deutsche Forschungsgemeinschaft
- National Natural Science Foundation of China (81125022, 81302693, 81661148049, U1501221)
- Guangzhou City (201506010023)
- Guangdong Province (2013B051000057)
- Special Financial Fund of Innovative Development of Marine Economic Demonstration Project (GD2012-D01-001)
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