Synthesis of the AB ring system of clifednamide utilizing Claisen rearrangement and Diels-Alder reaction as key steps.
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Authors
Loke, IngaBentzinger, Guillaume
Holz, Julia
Raja, Aruna
Bhasin, Aman
Sasse, Florenz
Köhn, Andreas
Schobert, Rainer
Laschat, Sabine
Issue Date
2016-01-21
Metadata
Show full item recordAbstract
In order to construct the functionalized AB ring system of clifednamide, member of the class of macrocyclic tetramic acid lactams, a synthesis was developed which utilized an Ireland-Claisen rearrangement and an intramolecular Diels-Alder reaction. Starting from di-O-isopropylidene-d-mannitol the allyl carboxylate precursor for the sigmatropic rearrangement was prepared. This rearrangement proceeded diastereoselectively only in the presence of an allyl silyl ether instead of the parent enone in the side chain, as suggested by deuteration experiments. A subsequent Diels-Alder reaction yielded the target ethyl hexahydro-1H-indene-carboxylate with high diastereoselectivity. Quantum-chemical investigations of this intramolecular Diels-Alder reaction support the proposed configuration of the final product.Citation
Synthesis of the AB ring system of clifednamide utilizing Claisen rearrangement and Diels-Alder reaction as key steps. 2016, 14 (3):884-94 Org. Biomol. Chem.Affiliation
Helmholtz-Zentrum für Infektionsforschung GmbH, Inhoffenstr. 7, 38124 Braunschweig, Germany.Journal
Organic & biomolecular chemistryPubMed ID
26599642Type
ArticleLanguage
enISSN
1477-0539ae974a485f413a2113503eed53cd6c53
10.1039/c5ob01491c
Scopus Count
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- Creative Commons
Except where otherwise noted, this item's license is described as http://creativecommons.org/licenses/by-nc-sa/4.0/
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