Transformations of lignans, part IV. Acid-catalysed rearrangements of gmelinol with BF3-etherate and study of a product with a unique lignan skeletonformed by further oxidation with DDQ

Authors
Ward, RS Pelter, A Venkateswarlu, R Kamakshi, C Subhash, PV Moinuddin, SGA Hursthouse, MB Coles, SJ Hibbs, DE
Citation
Rs. Ward et al., Transformations of lignans, part IV. Acid-catalysed rearrangements of gmelinol with BF3-etherate and study of a product with a unique lignan skeletonformed by further oxidation with DDQ, TETRAHEDRON, 55(45), 1999, pp. 13071-13086
Citations number
13
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
55
Issue
45
Year of publication
1999
Pages
13071 - 13086
Database
ISI
SICI code
0040-4020(19991105)55:45<13071:TOLPIA>2.0.ZU;2-9
Abstract
Reaction of gmelinol 1 with BF3-etherate followed by treatment with various additives gave two isomeric products 2 and 5 formed by rearrangement of th e 2,6-diaryl-3,7-dioxabicyclo[3.3.0]octane skeleton. Compounds 2 and 5 on o xidation with DDQ in trifluoroacetic acid or benzene produced enantiomers 8 and ent-8 respectively, which have a "distorted furofuran" skeleton. Compo und 5 on reduction with triethylsilane and BF3-etherate gave 13, which is i someric with di-O-methyl cycloolivil. (C) 1999 Elsevier Science Ltd. All ri ghts reserved.