Total synthesis and preliminary biological evaluation of cis-solamin isomers
Cecil, Alex R.L., Hu, Yulai, Vicent, María J., Duncan, Ruth and Brown, Richard C.D. (2004) Total synthesis and preliminary biological evaluation of cis-solamin isomers. Journal of Organic Chemistry, 69, (10), 3368-3374. (doi:10.1021/jo049909g)
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Official URL: http://dx.doi.org/10.1021/jo049909g
Description/Abstract
An efficient total synthesis of cis-solamin (1) has been achieved in 21% overall yield and with a longest linear sequence of just 11 steps from aldehyde S. A key feature of the approach was the use of asymmetric permanganate-promoted oxidative cyclization to introduce four of the five required stereocenters in a single step. The use of robust and chemoselective methodology meant that the use of protecting groups could be avoided during the assembly of cis-solamin (1) from the three fragments 23, 6, and 4. The methodology was also applied to the synthesis of three further cis-solamin isomers 2, ent-1, and ent-2. Cytotoxicity and hemolytic properties of cis-solamin isomers and synthetic intermediates are reported.
| Item Type: | Article |
|---|---|
| ISSN: | 0022-3263 (print) |
| Uncontrolled Keywords: | tetrahydrofuran-containing fragments, promoted oxidative cyclization, annonaceous acetogenins, stereoselective-synthesis, permanganateoxidation, modular synthesis, bioactive polyketides,rhenium(vii)oxides, natural-products, 1,5-dienes |
| Related URLs: | http://www.ncbi.nlm.nih.gov/en...s=15132544 http://dx.doi.org/10.1021/jo049909g |
| Subjects: | Q Science > QD Chemistry Q Science > QH Natural history > QH301 Biology |
| Divisions: | University Structure - Pre August 2011 > School of Chemistry |
| ePrint ID: | 20163 |
| URI: | http://eprints.soton.ac.uk/id/eprint/20163 |
| Deposited On: | 22 Feb 2006 |
| Last Modified: | 01 Apr 2012 02:11 |
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