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Transformations of lignans, part V. Reactions of DDQ with a gmelinol hydrogenolysis product and its derivatives

โœ Scribed by Revuru Venkateswarlu; Chakicherla Kamakshi; Syed G.A Moinuddin; Pithani V Subhash; Robert S Ward; Andrew Pelter; Michael B Hursthouse; Mark E Light

Book ID
104209683
Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
964 KB
Volume
55
Category
Article
ISSN
0040-4020

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โœฆ Synopsis

Hydrogenolysis of gmelinol 8 with sodium in liquid ammonia gives a triol 9, which is converted under various reaction conditions into a range of derivatives including the di-and tri-O-methyl ethers 10 and I1, a 3,4-dibenzyl-3-hydroxy-tetrahyckofuran 12, and its acetate 13. These derivatives undergo oxidative cyclisation with DDQ in acetic acid or trifluoroacetic acid to yield 1-aryRetralin, l-aryinaphthalene, dibenzocyclooctadiene and spirudienune derivatives in reactions which provide biomimetic analogies for biogenetic transformations of liguans.

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