doi: 10.1021/ol702440f.
Epub 2007 Dec 29.
Total synthesis of 7-deoxypancratistatin-1-carboxaldehyde and carboxylic acid via solvent-free intramolecular aziridine opening: phenanthrene to phenanthridone cyclization strategy
Affiliations
- PMID: 18163635
- DOI: 10.1021/ol702440f
Item in Clipboard
Total synthesis of 7-deoxypancratistatin-1-carboxaldehyde and carboxylic acid via solvent-free intramolecular aziridine opening: phenanthrene to phenanthridone cyclization strategy
Org Lett.
.
Abstract
Solid-state silica-gel-catalyzed opening of aziridine 6 provided phenanthrene 7, whose oxidative cleavage, recyclization, and further elaboration furnished the C-1 aldehyde and carboxylic acid derivatives of 7-deoxypancratistatin for potential analogue synthesis.
Similar articles
-
Chemoenzymatic synthesis of Amaryllidaceae constituents and biological evaluation of their C-1 analogues. The next generation synthesis of 7-deoxypancratistatin and trans-dihydrolycoricidine.J Org Chem. 2010 May 7;75(9):3069-84. doi: 10.1021/jo1003136. J Org Chem. 2010. PMID: 20373760 Free PMC article.
-
Synthesis of (+)-lycoricidine by the application of oxidative and regioselective ring-opening of aziridines.Org Lett. 2010 Jun 4;12(11):2544-7. doi: 10.1021/ol100755v. Org Lett. 2010. PMID: 20441205
-
Reactions of indole derivatives with oxiranes and aziridines on silica. Synthesis of beta-carbolin-1-one mimic of pancratistatin.J Org Chem. 2005 Apr 29;70(9):3490-9. doi: 10.1021/jo040292c. J Org Chem. 2005. PMID: 15844982
-
Synthesis of Amaryllidaceae Constituents and Unnatural Derivatives.Angew Chem Int Ed Engl. 2016 May 4;55(19):5642-91. doi: 10.1002/anie.201508227. Epub 2016 Mar 11. Angew Chem Int Ed Engl. 2016. PMID: 26969844 Review.
-
Applications of total synthesis toward the discovery of clinically useful anticancer agents.Chem Soc Rev. 2007 Aug;36(8):1207-26. doi: 10.1039/b611967k. Epub 2007 Jun 6. Chem Soc Rev. 2007. PMID: 17619682 Review.
Cited by
-
Chemoenzymatic synthesis of Amaryllidaceae constituents and biological evaluation of their C-1 analogues. The next generation synthesis of 7-deoxypancratistatin and trans-dihydrolycoricidine.J Org Chem. 2010 May 7;75(9):3069-84. doi: 10.1021/jo1003136. J Org Chem. 2010. PMID: 20373760 Free PMC article.
-
Antineoplastic agents. 454. Synthesis of the strong cancer cell growth inhibitors trans-dihydronarciclasine and 7-deoxy-trans-dihydronarciclasine (1a).J Nat Prod. 2009 Jul;72(7):1279-82. doi: 10.1021/np9001948. J Nat Prod. 2009. PMID: 19522518 Free PMC article.
-
Unnatural C-1 homologues of pancratistatin - Synthesis and promising biological activities.Can J Chem. 2012;90(11):932-943. doi: 10.1139/v2012-073. Epub 2012 Sep 19. Can J Chem. 2012. PMID: 28017970 Free PMC article.
-
Synthesis of C-1 homologues of pancratistatin and their preliminary biological evaluation.Bioorg Med Chem Lett. 2011 Aug 15;21(16):4750-2. doi: 10.1016/j.bmcl.2011.06.068. Epub 2011 Jun 22. Bioorg Med Chem Lett. 2011. PMID: 21757350 Free PMC article.
-
Stereoselective synthesis of trans-dihydronarciclasine derivatives containing a 1,4-benzodioxane moiety.Monatsh Chem. 2018;149(12):2265-2285. doi: 10.1007/s00706-018-2287-7. Epub 2018 Oct 26. Monatsh Chem. 2018. PMID: 32214482 Free PMC article.
Publication types
MeSH terms
Substances
LinkOut - more resources
Full Text Sources
Other Literature Sources
