An efficient route to the complex L-kedarosamine alpha-glycosidic ether 2, a synthetic precursor to kedarcidin chromophore, is described. Central to the route, which is suitable for the preparation of multigram amounts of material, is a short synthetic sequence from D-threonine to protected L-kedarosamine derivatives and methodology for their alpha-selective coupling with appropriate hydroxyl acceptors.
Download full-text PDF |
Source |
|---|---|
| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3176327 | PMC |
| http://dx.doi.org/10.1021/ol070450x | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
A convergent total synthesis of the kedarcidin chromophore: 20-years in the making.
J Antibiot (Tokyo)
June 2019
Department of Chemistry, Graduate School of Science, Tohoku University, Aza Aramaki, Aoba-ku, Sendai, 980-8578, Japan.
The kedarcidin chromophore is a formidible target for total synthesis. Herein, we describe a viable synthesis of this highly unstable natural product. This entailed the early introduction and gram-scale synthesis of 2-deoxysugar conjugates of both L-mycarose and L-kedarosamine.
View Article and Find Full Text PDFA new member of the 4-methylideneimidazole-5-one-containing aminomutase family from the enediyne kedarcidin biosynthetic pathway.
Proc Natl Acad Sci U S A
May 2013
Department of Chemistry, The Scripps Research Institute, Jupiter, FL 33458, USA.
4-Methylideneimidazole-5-one (MIO)-containing aminomutases catalyze the conversion of L-α-amino acids to β-amino acids with either an (R) or an (S) configuration. L-phenylalanine and L-tyrosine are the only two natural substrates identified to date. The enediyne chromophore of the chromoprotein antitumor antibiotic kedarcidin (KED) harbors an (R)-2-aza-3-chloro-β-tyrosine moiety reminiscent of the (S)-3-chloro-5-hydroxy-β-tyrosine moiety of the C-1027 enediyne chromophore, the biosynthesis of which uncovered the first known MIO-containing aminomutase, SgcC4.
View Article and Find Full Text PDFCloning and sequencing of the kedarcidin biosynthetic gene cluster from Streptoalloteichus sp. ATCC 53650 revealing new insights into biosynthesis of the enediyne family of antitumor antibiotics.
Mol Biosyst
March 2013
Department of Chemistry, The Scripps Research Institute, Jupiter, Florida 33458, USA.
Enediyne natural product biosynthesis is characterized by a convergence of multiple pathways, generating unique peripheral moieties that are appended onto the distinctive enediyne core. Kedarcidin (KED) possesses two unique peripheral moieties, a (R)-2-aza-3-chloro-β-tyrosine and an iso-propoxy-bearing 2-naphthonate moiety, as well as two deoxysugars. The appendage pattern of these peripheral moieties to the enediyne core in KED differs from the other enediynes studied to date with respect to stereochemical configuration.
View Article and Find Full Text PDFTotal synthesis of a protected aglycon of the kedarcidin chromophore.
Angew Chem Int Ed Engl
March 2009
Department of Chemistry, Graduate School of Science, Tohoku University, Sendai, Japan.
Secure route to the epoxybicyclo[7.3.0]dodecadienediyne core of the kedarcidin chromophore.
Chem Commun (Camb)
December 2008
Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980-8578, Japan.
Formation of an epoxide before 9-membered ring cyclization and SmI2 mediated reductive olefination in the presence of the epoxide successfully produced the epoxybicyclo[7.3.0]dodecadienediyne core of the kedarcidin chromophore.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!