First example of intramolecular [2π + 2π] alkene–arene photocyclization in the chromone series and its synthetic utility
✍ Scribed by Roman A. Valiulin; Andrei G. Kutateladze
- Publisher
- Elsevier Science
- Year
- 2010
- Tongue
- French
- Weight
- 801 KB
- Volume
- 51
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
Diels-Alder adducts of chromones are shown to undergo an intramolecular [2(pi)+2(pi)] alkene-arene photocyclization, leading to a versatile polycyclic diene, which is capable of dimerization or can be introduced into a high yielding photoprotolytic oxametathetic sequence. This allows for an expeditious growth of molecular complexity over a few experimentally simple steps with stereochemistry being defined and locked at the very first Diels-Alder step. The overall reaction can potentially be utilized in Diversity-Oriented Synthesis as it allows for three or more diversity inputs furnishing novel unique polycyclic scaffolds, which can readily be decorated with a variety of functionalities and aromatic/heterocyclic pendants.