Expanding the aplysinospin cascade through DNA-templated [2+2] photocycloaddition

Inspired by the unique ability of nucleic acids to template chemical transformations that are otherwise impossible in solution, we embarked on the generalisation of our DNA-templated [2+2] photo-induced homo- and heterodimerization of aplysinopsins. Our process ensures a straightforward access to cy...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2023-04, Vol.59 (28), p.4221-4224
Main Authors: Oger, Samuel, Duchemin, Nicolas, Bendiab, Yara Mayssa, Birlirakis, Nicolas, Skiredj, Adam, Rharrabti, Somia, Jullian, Jean-Christophe, Poupon, Erwan, Smietana, Michael, Arseniyadis, Stellios, Evanno, Laurent
Format: Article
Language:English
Subjects:
Biomimetics
Chemical Sciences
Cyclobutane
DNA
DNA Replication
Medicinal Chemistry
Natural products
Nucleic Acids
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Summary:Inspired by the unique ability of nucleic acids to template chemical transformations that are otherwise impossible in solution, we embarked on the generalisation of our DNA-templated [2+2] photo-induced homo- and heterodimerization of aplysinopsins. Our process ensures a straightforward access to cyclobutane containing natural products and analogues thereof. Most importantly, this conceptual biomimetic achievement presents interesting arguments to build a biosynthetic scenario. We report here a general and scalable method for the synthesis of cyclobutane-containing natural products and analogues thereof via a DNA-templated [2+2] photo-induced homo- and heterodimerization of aplysinopsins.
ISSN:1359-7345
1364-548X
DOI:10.1039/d3cc00673e