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Enantioselective synthesis of 2,2,5-Tri- and 2,2,5,5-tetrasubstituted tetrahydrofurans and synthesis of diketopiperazine containing natural products

A chiral vinyl sulfoxide has been developed that undergoes highly diastereoselective Dielsāˆ’Alder 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

Identiferoai:union.ndltd.org:UTEXAS/oai:repositories.lib.utexas.edu:2152/19501
Date18 February 2013
CreatorsBenjamin, Noah Meyer
Source SetsUniversity of Texas
Languageen_US
Detected LanguageEnglish
Formatapplication/pdf

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