𝔖 Bobbio Scriptorium
✦   LIBER   ✦

Stereospezifische Synthese einer neuen Morphin-Teilstruktur

✍ Scribed by Walter Haefliger; Edgar Klöppner

Publisher
John Wiley and Sons
Year
1982
Tongue
German
Weight
1019 KB
Volume
65
Category
Article
ISSN
0018-019X

No coin nor oath required. For personal study only.

✦ Synopsis

We describe here a synthesis of the morphine partial structures 28 and 36, and of their enantiomers, which uses 7‐methoxy‐benzofurancarboxylic acid as starting material. A key intermediate in this scheme is compound 15, which is converted, via 1,2‐ketone shift, into 22. This latter is stereospecifically reduced to the alcohol 24 and converted to the amide 25. The diastereomer of 25 is afforded by stereospecific introduction of a ethoxycarbonyl group in 15 to yield the β‐ketoester 31, followed by Curtius degradation of the acid 32 to the acylamine 34.

An efficient method for removal of the methoxy group in methoxy‐dihydro‐benzofurans is presented (Scheme 9), as is the functionalization of the N‐atom in 27 with concurrent complex formation between the free hydroxy group and boric‐acid. The aromatization of the furan ring (Scheme 10) with DDQ gave the expected benzofuran derivative 30.

📜 SIMILAR VOLUMES

Synthese von neuen Morphin-Teilstrukture
Synthese von neuen Morphin-Teilstrukturen des Typs 15,16-Secomorphinan
✍ László Révész 📂 Article 📅 1984 🏛 John Wiley and Sons 🌐 German ⚖ 337 KB

## Abstract **Synthesis of New Morphine Partial Structure 15,16‐Secomorphinan** The synthesis of a new morphine partial structure, 15,16‐secomorphinan, is described. One of the series, (±)‐15, 16‐secocyclorphan **(5)**, has the analgesic potency of morphine and exhibits good binding to the opiate

Synthese einer neuen Klasse lösungsmitte
Synthese einer neuen Klasse lösungsmittelabhängiger Fluoreszenzmarker
✍ James J. La Clair 📂 Article 📅 1998 🏛 John Wiley and Sons 🌐 English ⚖ 103 KB

Charge-Transfer(CT)-Marker wie 5-(Dimethylamino)naphthalin-1-sulfonyl(Dansyl)-chlorid wurden in groûem Ausmaû beim Nachweis sowie bei der Charakterisierung und Lokalisierung von Kohlenhydraten, Phospolipiden, Proteinen, Oligonucleotiden sowie zahlreichen anderen synthetischen und natürlich vorkommen

Versuche zu einer neuen Synthese von Cep
Versuche zu einer neuen Synthese von Cephem-Verbindungen
✍ Theodor Petrzilka; Charles Fehr; Gérard Schmid 📂 Article 📅 1976 🏛 John Wiley and Sons 🌐 German ⚖ 682 KB

**Contributions for a new synthesis of Cephem compounds.** Compounds **10** and **12** of type **2** were synthesized by pyrolysis of phenoxy‐urethanes **9** and **11**. The unsaturated side chain was synthesized by __Michael__‐addition of **7** to propiolic acid. Intramolecular [2 + 2]‐Cycloadditi