Synthesis of a Tetracyclo [4.4.0.02,4.03,8]decanone via Intramolecular Reductive Coupling

✍ Scribed by Paul Margaretha; Paul Tissot

• Book ID: 102252372
• Publisher: John Wiley and Sons
• Year: 1982
• Tongue: German
• Weight: 207 KB
• Volume: 65
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/hlca.19820650629

✦ Synopsis

Abstract

The reduction of cis‐4 a‐methyl‐1,2,4a,7,8,8 a‐hexahydronaphthalene‐2,7‐dione (1) was studied by cyclic voltammetry and product analysis. On a preparative scale, 6‐hydroxy‐3‐methyltetracyclo[4.4.0.0^2,4^.0^3,8^]decan‐10‐one (2) was obtained in 22% yield via an intramolecular hydrodimerization/aldol reaction sequence. The CV. results (Hg, DMF) suggest that the cyclopropane ring is formed after the first electron transfer by coupling of the anion radical with the second C. C‐double bond.