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Synthetic Studies toward Sordarin: Building Blocks for the Terpenoid Core and for Analogues Thereof

TitleSynthetic Studies toward Sordarin: Building Blocks for the Terpenoid Core and for Analogues Thereof
Publication TypeJournal Article
Year of Publication2009
AuthorsSchule, A, Liang, H, Vors, JP, Ciufolini, MA
JournalJournal of Organic Chemistry
Volume74
Pagination1587-1597
Date PublishedFeb
Type of ArticleArticle
ISBN Number0022-3263
KeywordsANTIFUNGAL SORDARINS, BAYLIS-HILLMAN REACTION, DERIVATIVES, ELONGATION-FACTOR 2, ENOLATE FORMATION, FUNGAL PROTEIN-SYNTHESIS, KETONE ENOLIZATION, LITHIUM DIALKYLAMIDES, RING-CLOSURE, SODIUM-BOROHYDRIDE
Abstract

Avenues to bi- and tricyclic building blocks for the elaboration of sordaricin and its analogues are described. The target molecules were obtained through inter- and intramolecular Diels-Alder reactions of a number of previously unknown cyclopentadienes. Unusual properties of 3-cyanoenones and 1-cyanocyclopentadienes have been unveiled and circumvented.

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