Abstract
The synthesis of naturally occurring furan derivatives rehmanones A, B, and C is described. Diverse alternative synthetic strategies were developed for the preparation of these natural products. Conjugate addition of a furan to captodative alkene 1-acetylvinyl 4-nitrobenzoate was carried out under Lewis acid catalysis to give the corresponding adduct, which was transformed into rehmanones B and C in three and two steps, respectively. They were also prepared by condensation of acetone with the key furan-2-carbaldehyde intermediates, which could be readily obtained from D-fructose. The bis-furan rehmanone A was not only obtained in a one-step procedure by a double condensation of acetone with 5-(methoxymethyl)furan-2-carbaldehyde, but by condensing the latter with rehmanone B in high overall yields.
Original language | English |
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Pages (from-to) | 1023-1028 |
Number of pages | 6 |
Journal | Synthesis (Germany) |
Issue number | 7 |
DOIs | |
State | Published - 1 Apr 2008 |
Keywords
- Captodative alkenes
- Condensation
- Conjugate addition
- Lewis acids
- Rehmanones A, B, and C