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A Short Synthesis of (±)-(cis-6-Methyltetrahydropyran-2-yl)Acetic Acid, a Constituent of Civet

✍ Scribed by Cornelius Nussbaumer; Georg Fráter


Publisher
John Wiley and Sons
Year
1987
Tongue
German
Weight
386 KB
Volume
70
Category
Article
ISSN
0018-019X

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✦ Synopsis


Similar cyclizations to tetrahydropyrans are known [lo] to occur when 4-methyl-4-pentcn-2-01 Is condensed with aldehydes under acidic conditions (Kriewitz-Prim reaction [l I]).

A /I-alkenyloxyacrylate cyclization has already found use in a stereoselective synthesis of (i)-cis-a-irone [ 161.


📜 SIMILAR VOLUMES


Syntheses of (+)-(S,S)-(cis-6-Methyltetr
✍ Dieter Seebach; Manat Phmakotr 📂 Article 📅 1979 🏛 John Wiley and Sons 🌐 German ⚖ 241 KB

## Abstract The Li/K‐derivative **6** is used to synthesize the title compounds (**3a** and **4a**) in enantiomerically pure form from (−)‐(__S__)‐propylene epoxide. The C,C bond forming key step leading to the hydroxyketone 7 is followed by cyclization (→, **8**), Beckmann cleavage (→ **9b**) and