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Design, Total Synthesis, and Evaluation of C(13)−C(14) Cyclopropane Analogues of (+)-Discodermolide

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journal contribution
posted on 13.10.2005, 00:00 by Amos B. Smith, Ming Xian, Fenghua Liu
The design, total synthesis, and biological evaluation of two C(13)−C(14)-cyclopropyl analogues [(+)-1 and (+)-2] of (+)-discodermolide have been achieved. Key features of the syntheses include highly stereoselective, hydroxyl-directed cyclopropanations of vinyl iodides and higher order cuprate-mediated cross-coupling reactions between cyclopropyl iodides and alkyl iodides. Biological evaluation revealed that neither orientation of the cyclopropyl methylene completely substitutes for the C(14) methyl found in (+)-discodermolide (3).