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
✍ Scribed by Robert S Ward; Andrew Pelter; Revuru Venkateswarlu; Chakicherla Kamakshi; Pithani V Subhash; Syed G.A Moinuddin; Michael B Hursthouse; Simon J Coles; David E Hibbs
- Publisher
- Elsevier Science
- Year
- 1999
- Tongue
- French
- Weight
- 725 KB
- Volume
- 55
- Category
- Article
- ISSN
- 0040-4020
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✦ Synopsis
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 $ and ent-8 respectively, which have a "distorted forofuran" skeleton. Compound S on reduction with triethylsilane and BF3-etherate gave 13, which is isonleric with di-O-methyl cyclonlivil.