Total Synthesis of (+)‐Cochlearol B by an Approach Based on a Catellani Reaction and Visible‐Light‐Enabled [2+2] Cycloaddition

A 14‐step synthesis of (+)‐cochlearol B is reported. This renoprotective meroterpenoid features a unique core structure containing a densely substituted cyclobutane ring with three stereocenters. Our strategy employed an organocatalytic Kabbe condensation in route to the key chromenyl triflate. A su...

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Bibliographic Details
Published in:Angewandte Chemie 2022-08, Vol.134 (31), p.n/a
Main Authors: Richardson, Alistair D., Vogel, Trenton R., Traficante, Emily F., Glover, Kason J., Schindler, Corinna S.
Format: Article
Language:English
Subjects:
[2+2] Photocycloaddition
Catellani Reaction
Chemistry
Cycloaddition
Cyclobutane
Heptanes
Meroterpenoids
Total Synthesis
Visible Light
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Summary:A 14‐step synthesis of (+)‐cochlearol B is reported. This renoprotective meroterpenoid features a unique core structure containing a densely substituted cyclobutane ring with three stereocenters. Our strategy employed an organocatalytic Kabbe condensation in route to the key chromenyl triflate. A subsequent Catellani reaction incorporated the remaining carbon atoms featured in the skeleton of cochlearol B. An ensuing visible‐light‐mediated [2+2] photocycloaddition closed the cyclobutane and formed the central bicyclo[3.2.0]heptane core. Notably, careful design and tuning of the Catellani and photocycloaddition reactions proved crucial in overcoming undesired reactivity, including cyclopropanation reactions and [4+2] cycloadditions. A 14‐step approach to (+)‐cochlearol B is reported. The strategy involves an organocatalytic Kabbe condensation, Catellani reaction, and visible‐light‐mediated [2+2] cycloaddition to rapidly access the core of this natural product. Careful design and tuning of the Catellani and photocycloaddition reactions proved crucial in overcoming undesired reactivity, including cyclopropanation reactions, and [4+2] cycloadditions.
ISSN:0044-8249
1521-3757
DOI:10.1002/ange.202201213