Starting from 2,3-dihydrofuran (7) we prepared aldehyde (5) which, in a [4+2] cycloaddition reaction with the tryptamine derivative (4) gave, as a final step, compound (10) having a D-seco-aspidospermane skeleton. We synthesized (±)-14-epi-deethylibophyllidine (3) via the mesylate (12) of alcohol (11) which had been obtained from 10, whereas the cyclization of the benzoate ester (15) resulted in (±)-deethylibophyllidine (2). We have managed to build up (±)-2 via the tetracyclic intermediates (16) and (20).
|Number of pages||17|
|Publication status||Published - Nov 1 2006|
ASJC Scopus subject areas
- Analytical Chemistry
- Organic Chemistry