✦ LIBER ✦

A formal synthesis to (+)-nephrosteranic acid from chiral nitroalkyl derivatives

✍ Scribed by Cleber B. Barreto Jr.; Vera L. Patrocinio Pereira

Publisher: Elsevier Science
Year: 2009
Tongue: French
Weight: 338 KB
Volume: 50
Category: Article
ISSN: 0040-4039
DOI: 10.1016/j.tetlet.2009.08.087

No coin nor oath required. For personal study only.

✦ Synopsis

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%), derived from D-(+)-mannitol.

📜 SIMILAR VOLUMES

Aldol Reactions of Dioxanes Derived from

Aldol Reactions of Dioxanes Derived from Tartaric Acid. A Total Synthesis of (+)-Nephrosteranic Acid.

✍ M. Teresa Barros; Christopher D. Maycock; M. Rita Ventura 📂 Article 📅 2004 🏛 John Wiley and Sons ⚖ 78 KB 👁 1 views

From phenylaziridine to phenylkainoids.

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

✍ Marie-Reine Schneider; Philippe Klotz; Ioana Ungureanu; André Mann; Camille-Geor 📂 Article 📅 1999 🏛 Elsevier Science 🌐 French ⚖ 252 KB

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 dou

Regio- and Stereocontrolled Conjugate Ra

Regio- and Stereocontrolled Conjugate Radical Addition to a Desymmetrized Fumarate Derivative: An Efficient Synthesis of (−)-Nephrosteranic Acid and (−)-Roccellaric Acid

✍ Prof. Mukund P. Sibi; Dr. Jianguo Ji 📂 Article 📅 1997 🏛 John Wiley and Sons 🌐 English ⚖ 416 KB 👁 2 views

ChemInform Abstract: From Phenylaziridin

ChemInform Abstract: From Phenylaziridine to Phenylkainoids. A Formal Synthesis of (.+-.)-Phenylkainic Acid.

✍ Marie-Reine Schneider; Philippe Klotz; Ioana Ungureanu; Andre Mann; Camille-Geor 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 34 KB

ChemInform Abstract: Regio- and Stereoco

ChemInform Abstract: Regio- and Stereocontrolled Conjugated Radical Addition to a Desymmetrized Fumarate Derivative: An Efficient Synthesis of (-)- Nephrosteranic Acid and (-)-Roccellaric Acid.

✍ M. P. SIBI; J. JI 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 31 KB 👁 2 views

Chiral 1,3,6-Trisubstituted 2,4-Dioxohex

Chiral 1,3,6-Trisubstituted 2,4-Dioxohexahydropyrimidines: A Convenient Stereoselective Synthesis from Aspartic Acid Derivatives.

✍ Rosario Patino-Molina; Ivan Cubero-Lajo; M. Jesus Perez de Vega; M. Teresa Garci 📂 Article 📅 2007 🏛 John Wiley and Sons ⚖ 21 KB