Details

Autor(en) / Beteiligte

• Piotrowski, Mathew L.
• Kerr, Michael A.

Titel

Synthesis of (±)‐β‐Allokainic Acid

Ist Teil von

• European journal of organic chemistry, 2019-06, Vol.2019 (20), p.3122-3126

Ort / Verlag

Weinheim: Wiley Subscription Services, Inc

Erscheinungsjahr

2019

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• The total synthesis of kainoid alkaloid, (+/–)‐β‐allokainic acid is reported. The key step is a vinylogous Cloke–Wilson rearrangement followed by Lewis acid and transition metal induced transformations to prepare a highly functionalized pyrrolidine suitable for conversion to the target molecule. A vinylogous Cloke–Wilsom rearrangement of suitable donor–acceptor cyclopropane allows for the formation of a 2,5‐dihydrooxepine which, in turn, is easily converted to a dihydropyrrole. A series of straightforward transformations provides an expedient synthesis of (+/–)‐β‐allokainic acid.