Enantioselective Synthesis of Photodynamic Rubellin Anthraquinone Dimers
Biological and Biomimetic Chemistry
Final Report Abstract
In summary, we achieved to synthesize the indane core characteristic to the rubellin family of anthraquinone dimer, however without being able to synthesize one of the natural products of this group, despite thoroughly targeting torrubiellin A as the first member of this family. The electronic and steric requirements for the fulfillment of the photoinduced radical cyclization represent a strong limitation of the executed pathway and allows a very restricted scope of the synthesized rubellin-like molecules. These results are to date not exploitable in the chemical or the pharmaceutical industries. Further endeavours using non-photochemical radical triggers can be envisaged as well as the use of metals of chelators stabilizing the initial radical species. Furthermore, an indirect synthesis of the natural product can be in question, by converting the obtained torrubiellin analogue into torrubiellin A by regioand stereoselective reduction. Initial chemical biological or medicinal chemical investigations can be pursued using the non-natural torrubiellin analogue, as those retain the photophysical properties of their natural counterparts for photodynamic therapy.
Publications
- 6-Step Syntheses of (+)-30-epi-, (-)-6-epi-, 6,30-epi-13,14-Didehydroxyisogarcinol and 6,30-epi-Garcimultiflorone A Utilizing a Highly Diastereoselective, Lewis Acid-Controlled Cyclization; J. Am. Chem. Soc. 2016, 138, 14789–14797
J. H. Boyce, V. Eschenbrenner-Lux, J. A. Porco, Jr.
(See online at https://doi.org/10.1021/jacs.6b09727) - Asymmetric Syntheses of the Flavonoid Diels-Alder Natural Products Sanggenons C and O; J. Am. Chem. Soc. 2016, 138, 798–801
C. Qi, Y. Xiong, V. Eschenbrenner-Lux, H. Cong, and J. A. Porco, Jr.
(See online at https://doi.org/10.1016/j.procir.2015.12.015)
