Journal article
Design, total synthesis, and evaluation of C13-C14 cyclopropane analogues of (+)-discodermolide
Organic letters, Vol.7(21), pp.4613-4616
10/13/2005
Handle:
https://hdl.handle.net/2376/110610
PMID: 16209492
Abstract
[structure: see text] The design, total synthesis, and biological evaluation of two C13-C14-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 C14 methyl found in (+)-discodermolide (3).
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Details
- Title
- Design, total synthesis, and evaluation of C13-C14 cyclopropane analogues of (+)-discodermolide
- Creators
- Amos B Smith, 3rd - Department of Chemistry, Monell Chemical Senses Center, and Laboratory for Research on the Structure of Matter, University of Pennsylvania, Philadelphia, Pennsylvania 19104, USA. smithab@sas.upenn.eduMing XianFenghua Liu
- Publication Details
- Organic letters, Vol.7(21), pp.4613-4616
- Academic Unit
- Chemistry, Department of
- Publisher
- United States
- Grant note
- GM-29028 / NIGMS NIH HHS
- Identifiers
- 99900547493901842
- Language
- English
- Resource Type
- Journal article