𝔖 Bobbio Scriptorium
✦   LIBER   ✦

From phenylaziridine to phenylkainoids. A formal synthesis of (±)-phenylkainic acid

✍ Scribed by Marie-Reine Schneider; Philippe Klotz; Ioana Ungureanu; André Mann; Camille-Georges Wermuth

Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
252 KB
Volume
40
Category
Article
ISSN
0040-4039

No coin nor oath required. For personal study only.

✦ Synopsis

The condensation of phenylaziridines (3a/3b) with 3-cyclopentenylsilane (4) in presence of BF3.Et20 yielded amino-cyclopentenyl adducts (Sa-8a) and (Sb-8b). Heterocyclisation of the 03-amino-olefins assisted by Pd(OAc)2 afforded the azabicyclo adducts 2a/2'a and 2b/2'b. Oxidation of the internal double bond, followed by epimerization at C(2) was realized by KH in presence of 18-crown-6 yielding 11, the fully protected phenylkainic acid.

📜 SIMILAR VOLUMES

A formal synthesis to (+)-nephrosteranic
A formal synthesis to (+)-nephrosteranic acid from chiral nitroalkyl derivatives
✍ Cleber B. Barreto Jr.; Vera L. Patrocinio Pereira 📂 Article 📅 2009 🏛 Elsevier Science 🌐 French ⚖ 338 KB

A concise and versatile formal synthesis to (+)-nephrosteranic acid was accomplished from a common nitroderivative 2 in a sequence of six steps. The adduct 2 was obtained via a highly syn-diastereoselective conjugate addition of 1-dodecyl nitronate ion to chiral enoate Z-5 (yield = 80%; de = 95%), d