Synthesis of bridged ring systems related to clovene

✍ Scribed by N.G. Kundu; S.L. Mukherjee; P.C. Dutta

• Publisher: Elsevier Science
• Year: 1962
• Tongue: French
• Weight: 133 KB
• Volume: 3
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)70920-8

✦ Synopsis

IN view of a recent publication by Murray et al.', we are prompted to report our results on a synthetic approach to the ring-system related to clovene. The novelty of the present communication is the synthesis of a hydrindane derivative (XII) with appropriate functional groups and having the desired stereochemistry at all the asymmetric centres. The bicyclic ketone V was singled out to be a potential intermediate for this purpose in view of the successful observations made in this laboratory in a related field and the synthesis of the ketone was achieved through the following steps. The conjugate addition of methylmagnesium iodide to ethyl a-cyano-p-(e-methoxyphenyl)-crotonate I 2 was effected in the presence of cuprous iodide3 resulting in the formation of the product II, b.p. 167-174'/0.6 mm. p-Methyl-p-(E-methoxyphenyl)-butyric acid (III), m.p. 89-90' obtained on hydrolysis and decarboxylation was cyclized with polyphosphoric acid4 to the indanone IV, red 2.4-dinitrophenvlhvdrazone (m.p. 266-267').

* Analysis of all the compounds described corresponded to the calculated values.