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Oxidative transformations of lignans - reactions of dihydrocubebin and a derivative with DDQ

โœ Scribed by Andrew Pelter; Robert S. Ward; Revuru Venkateswarlu; Chakicherla Kamakshi

Book ID
104203940
Publisher
Elsevier Science
Year
1991
Tongue
French
Weight
487 KB
Volume
47
Category
Article
ISSN
0040-4020

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โœฆ Synopsis

Treatment of dihydrocubebin (1) with DDQ in acetic acid gives the 2-aryltetrahydrofuran (3) while with DDQ in trifluoroacetic acid it affords the isomeric dibenzocyclooctadiene (5). Treatment of the 3,4-dibenzyltetrahydrofuran (2), obtained by cyclisation of (1), with DDQ in acetic acid gives a mixture of the acetoxy compound ( 8) and the aryl tetraiin (9), while with DDQ in tfifluoroacetic acid it gives the dibenzocyclooctadiene (10). The structural elucidation of these products is described and mechanisms for their formation are presented.

๐Ÿ“œ SIMILAR VOLUMES

Transformations of lignans, part V. Reac
Transformations of lignans, part V. Reactions of DDQ with a gmelinol hydrogenolysis product and its derivatives
โœ Revuru Venkateswarlu; Chakicherla Kamakshi; Syed G.A Moinuddin; Pithani V Subhas ๐Ÿ“‚ Article ๐Ÿ“… 1999 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 964 KB

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

Transformations of lignans, part IV. Aci
Transformations of lignans, part IV. Acid-catalysed rearrangements of gmelinol with BF3-etherate and study of a product with a unique lignan skeleton formed by further oxidation with DDQ
โœ Robert S Ward; Andrew Pelter; Revuru Venkateswarlu; Chakicherla Kamakshi; Pithan ๐Ÿ“‚ Article ๐Ÿ“… 1999 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 725 KB

Reaction of gmelinol 1 with BF3-etherate followed by treatment with various additives gave two isomeric woducts 2 and $ formed by rearrangement of the 2,6-diaryl-3,7-dioxabizyclo[3.3.0]oetane skeleton. Compounds 2 and S on oxidation with DDQ in trifluor~\_\_~ic acid or benzene produced enantiomers $