Details

Autor(en) / Beteiligte

• Richardson, Alistair D.
• Vogel, Trenton R.
• Traficante, Emily F.
• Glover, Kason J.
• Schindler, Corinna S.

Titel

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

Ist Teil von

• Angewandte Chemie (International ed.), 2022-08, Vol.61 (31), p.e202201213-n/a

Auflage

International ed. in English

Ort / Verlag

Germany: Wiley Subscription Services, Inc

Erscheinungsjahr

2022

Link zum Volltext

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• 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.