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Efficient Synthesis of (−)-(R)-Muscone by Enantioselective Protonation

✍ Scribed by Charles Fehr; José Galindo; Iris Farris; Ana Cuenca

Publisher
John Wiley and Sons
Year
2004
Tongue
German
Weight
249 KB
Volume
87
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

A new synthesis of (−)‐(R)‐muscone ((R)‐1) by means of enantioselective protonation of a bicyclic ketone enolate as the key step (see 6→(S)‐4 in Scheme 2) is presented. The C~15~ macrocyclic system is obtained by ozonolysis (Scheme 7).

📜 SIMILAR VOLUMES

ChemInform Abstract: Ring Closing Metath
ChemInform Abstract: Ring Closing Metathesis Guided Synthesis of (R)-(-)-Muscone.
✍ V. P. KAMAT; H. HAGIWARA; T. SUZUKI; M. ANDO 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 32 KB

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Macrocyclic Ring Closure of OH-assisted
Macrocyclic Ring Closure of OH-assisted Prins Reaction. A new and efficient synthesis of (R,S)-muscone
✍ Karl H. Schulte-Elte; Arnold Hauser; Günther Ohloff 📂 Article 📅 1979 🏛 John Wiley and Sons 🌐 German ⚖ 489 KB

## Abstract A new strategy for the synthesis of muscone **(1)** using the OH‐assisted __Prins__ reaction for macrocyclic ring closure has been developed. The monoacetal **4** of (__Z__,__E__)‐4,8‐dodecadienedial **(3)**, easily obtainable from (__Z__,__E__,__E__)‐1,5,9‐cyclododecatriene **(2)**, is