Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 61, Issue 31, Pages -Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202201213
Keywords
Catellani Reaction; Meroterpenoids; Total Synthesis; Visible Light; [2+2] Photocycloaddition
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Funding
- National Science Foundation [NSF CHE-1654223]
- Alfred P. Sloan Foundation
- David and Lucile Packard Foundation
- Camille and Henry Dreyfus Foundation
- BMS
- Rackham Graduate School of the University of Michigan
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A 14-step synthesis of (+)-cochlearol B, a renoprotective meroterpenoid, was reported. The synthesis involves the use of organocatalytic Kabbe condensation, Catellani reaction, and visible-light-mediated photocycloaddition. The synthesis features a unique core structure with a densely substituted cyclobutane ring.
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.
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