Abstract
A new synthesis of the indole alkaloid (-)-suaveoline from L-tryptophan is reported (overall yield ca. 14%). Key synthetic steps include a high yielding cis-specific Pictet-Spengler reaction, a one-pot Horner-Wadsworth-Emmons and alkylation procedure, a vinylogous Thorpe cyclisation and the direct formation of a 3,4,5-trisubstituted pyridine from a 1,5-dinitrile. The direct conversion of ajmaline to semi-synthetic suaveoline is also described. © The Royal Society of Chemistry 2000.
| Original language | English |
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| Pages (from-to) | 3578-3583 |
| Number of pages | 6 |
| Journal | Journal of the Chemical Society, Perkin Transactions 1 |
| Issue number | 21 |
| DOIs | |
| Publication status | Published - 2000 |