Skeletal rearrangement of furanoeremophilane-6β,10β-diol into farfugin A and farfugin B
✍ Scribed by Masahiro Tada; Yoshiaki Tanahashi; Yoshihiko Moriyama; Takeyoshi Takahashi
- Book ID
- 104237033
- Publisher
- Elsevier Science
- Year
- 1972
- Tongue
- French
- Weight
- 189 KB
- Volume
- 13
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
During the course of the structural investigation of furanoeremophilane-6B, lOS-diol (1, R = H),l) we have found that ;1 (R = H) is readily transformed into farfugin A (2)2), farfugin B (z)2) and another benzofuran (4) on dehydration with POc13.
We wish to report here the mechanism of these skeletal rearrangements. Treatment of 1 (R = H) [C15H2203, m.p. 1X", [a)D + 58'(EtOH)) with WC13 in pyridine at 110' under N2 gave rise to three benzofuran derivatives; 2 (ClgH180, m.p. 78 -7v", la)D + 32'(EtOH); yield after isolation 23 %], 2 [C15H180, an oil; Y. 34 %] and 4 (Y. 15 %), t wo of which were identified as farfugin A and B 2) by comparison of their spectral data. The third one, l5 lv C H OCl, a colorless oil, ia)D -20'(EtOH), was found to be 6-(&chloropentyl)-3,5_dimethylbenzofuran (4)