Synthesis of rocaglamide natural products via photochemical generation of oxidopyrylium species
First Claim
1. A method comprising:
- photochemically generating an oxidopyrylium species from a 3-hydroxychromone derivative; and
performing a cycloaddition reaction between the oxidopyrylium species and a dipolarophile to form a cycloadduct.
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Abstract
The present invention provides new strategies for the synthesis of compounds of the rocaglamide family and related natural products. In particular, the new biomimetic synthetic approach involves photochemical generation of an oxidopyrylium species from a 3-hydroxychromone derivative followed by 1,3-dipolar cycloaddition of the oxidopyrylium species to a dipolarophile. This approach can be used for the formation of adducts containing an aglain core structure. Methods for the conversion of aglain core structures to aglain, rocaglamide and forbaglin ring systems are also provided. The present invention also relates to the use of rocaglamide/aglain/forbaglin derivatives for the manufacture of medicaments for use in the treatment of cancer or cancerous conditions, disorders associated with cellular hyperproliferation, or NF-κB-dependent conditions.
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Citations
31 Claims
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1. A method comprising:
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photochemically generating an oxidopyrylium species from a 3-hydroxychromone derivative; and performing a cycloaddition reaction between the oxidopyrylium species and a dipolarophile to form a cycloadduct. - View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31)
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Specification