Synthesis of eupomatilone-6 and assignment of its absolute configuration

TitleSynthesis of eupomatilone-6 and assignment of its absolute configuration
Publication TypeJournal Article
Year of Publication2005
AuthorsGurjar, MK, Karumudi, B, Ramana, CV
JournalJournal of Organic Chemistry
Date PublishedNOV
Type of ArticleArticle

[GRAPHICS] The Zn-mediated Barbier reaction of the biarylaldehyde 8 with crotyl bromide followed by hydroboration and oxidation provided the gamma-butyrolactones 4 and 5. The stereoselective installation of methyl group at C-3 by using LiHMDS and MeI completed the synthesis of racemic eupomatilone-6 (2) and its diastereomer 3. The spectroscopic data of 2 was in fall agreement with reported spectra of natural product, thus confirming the revised relative configuration of eupomatilone-6. Similarly, an optically active (3R,4R,5S)-isomer of eupomatilone-6 (23) was prepared in which the aldol reaction with thiazolidinethione as a chiral auxiliary was employed as a key step. On the basis of the spectroscopic data and optical rotation values of 23, the absolute configuration of eupomatilone-6 was proposed.

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Organic Chemistry