A chiral vinyl sulfoxide has been developed that undergoes highly diastereoselective DielsāAlder cycloadditions with various substituted furans in excellent yield. The cycloadducts can be stereoselectively transformed into tetrasubstituted tetrahydrofurans via ring-opening metathesis/cross-metathesis or oxidative cleavage and refunctionalization.
A partial synthesis of the bioactive diketopiperazine containing natural product gliocladin C was achieved in nine steps, and 13.4% overall yield. The synthesis featured several novel transformations including the construction of the core structure by an elimination and nucleophilic addition sequence, followed by a Lewis acid promoted coupling with indole giving the key quaternary oxindole intermediate. A new protocol for intramolecular reductive coupling of the oxoindole and bis-unsaturated diketopiperazine led to successful construction of the hexacyclic skeleton. / text
| Identifer | oai:union.ndltd.org:UTEXAS/oai:repositories.lib.utexas.edu:2152/19501 |
| Date | 18 February 2013 |
| Creators | Benjamin, Noah Meyer |
| Source Sets | University of Texas |
| Language | en_US |
| Detected Language | English |
| Format | application/pdf |
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