Abstract
Readily available methyl 3-formylindol-2-ylacetate and N-tosyl-4-chloro-3- piperidone oxime have been used to construct the tetracyclic skeleton of the apparicine class of monoterpene indole alkaloids in only four steps in 80% overall yield. Key transformations in this convergent approach involve use of an intermolecular ester enolate/nitrosoalkene conjugate addition to form the C-15/16 bond, followed by a reductive cyclization to construct the C-ring of the tetracycle.
Original language | English (US) |
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Pages (from-to) | 6389-6393 |
Number of pages | 5 |
Journal | Journal of Organic Chemistry |
Volume | 79 |
Issue number | 13 |
DOIs | |
State | Published - Jul 3 2014 |
All Science Journal Classification (ASJC) codes
- Organic Chemistry