Ghosh, Shibaji K., Somanadhan, Brinda, Tan, Kevin S.-W. , Butler, Mark S. and Lear, Martin J. (2012) Absolute configuration and total synthesis of a novel antimalarial lipopeptide by the de novo preparation of chiral nonproteinogenic amino acids. Organic Letters, 14 (6). pp. 1560-1563. ISSN 1523-7060
Full content URL: http://dx.doi.org/10.1021/ol300293a
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| Item Type: | Article |
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| Item Status: | Live Archive |
Abstract
The absolute configuration (via degradation and Marfey’s derivatization studies) and the total synthesis of a novel antimalarial lipid-peptide isolated from Streptomyces sp. (IC50 = 0.8 μM, Plasmodium falciparum 3D7) is disclosed. To this end, versatile stereocontrolled routes to nonproteinogenic amino acids (via catalytic Mannich, Sharpless methods) and enantiomeric trans fatty acids (via Evans alkylation, Kocienski�-Julia olefination) have been developed.
| Keywords: | total synthesis, antimalarial, Natural Product, Amino acids |
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| Subjects: | F Physical Sciences > F160 Organic Chemistry |
| Divisions: | College of Science > School of Chemistry |
| ID Code: | 17103 |
| Deposited On: | 16 Apr 2015 14:26 |
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