doi: 10.1021/ol070889p.
Epub 2007 May 12.
Synthesis of DEFG ring of complestatin and chloropeptin I: highly atropdiastereoselective macrocyclization by intramolecular Suzuki-Miyaura reaction
Affiliations
- PMID: 17497871
- DOI: 10.1021/ol070889p
Item in Clipboard
Synthesis of DEFG ring of complestatin and chloropeptin I: highly atropdiastereoselective macrocyclization by intramolecular Suzuki-Miyaura reaction
Org Lett.
.
Abstract
Palladium-catalyzed intramolecular Suzuki-Miyaura reaction of linear tripeptide (23) afforded the 16-membered DEFG ring of complestatin (3) in good yield with an excellent atropdiastereoselectivity. Acidic treatment of 3 triggers a stereospecific rearrangement leading to the corresponding DEFG ring 4 of chloropeptin I.
Similar articles
-
Synthesis of diastereomers of complestatin and chloropeptin I: substrate-dependent atropstereoselectivity of the intramolecular Suzuki-Miyaura reaction.Angew Chem Int Ed Engl. 2008;47(22):4167-72. doi: 10.1002/anie.200800599. Angew Chem Int Ed Engl. 2008. PMID: 18404759 No abstract available.
-
Total synthesis of chloropeptin II (complestatin) and chloropeptin I.J Am Chem Soc. 2009 Nov 11;131(44):16036-8. doi: 10.1021/ja907193b. J Am Chem Soc. 2009. PMID: 19839632 Free PMC article.
-
Total synthesis of complestatin (chloropeptin II).Angew Chem Int Ed Engl. 2010 Mar 8;49(11):2018-22. doi: 10.1002/anie.200906797. Angew Chem Int Ed Engl. 2010. PMID: 20148426 No abstract available.
-
Access to macrocycles with an endo aryl ether and an endo aryl-aryl bond, development and application.Chimia (Aarau). 2011;65(3):168-74. doi: 10.2533/chimia.2011.168. Chimia (Aarau). 2011. PMID: 21528652 Review.
-
Contemporary strategies for peptide macrocyclization.Nat Chem. 2011 Jun 23;3(7):509-24. doi: 10.1038/nchem.1062. Nat Chem. 2011. PMID: 21697871 Review.
Cited by
-
Organotrifluoroborates and monocoordinated palladium complexes as catalysts--a perfect combination for Suzuki-Miyaura coupling.Angew Chem Int Ed Engl. 2009;48(49):9240-61. doi: 10.1002/anie.200904306. Angew Chem Int Ed Engl. 2009. PMID: 19899086 Free PMC article.
-
Boron Accumulation in Brain Tumor Cells through Boc-Protected Tryptophan as a Carrier for Boron Neutron Capture Therapy.ACS Med Chem Lett. 2020 Mar 16;11(4):589-596. doi: 10.1021/acsmedchemlett.0c00064. eCollection 2020 Apr 9. ACS Med Chem Lett. 2020. PMID: 32292568 Free PMC article.
-
Total synthesis of (+)-superstolide A.J Org Chem. 2008 Dec 19;73(24):9657-67. doi: 10.1021/jo801794s. J Org Chem. 2008. PMID: 18956845 Free PMC article.
-
Identification of a small molecule that induces ATG5-and-cathepsin-l-dependent cell death and modulates polyglutamine toxicity.Exp Cell Res. 2013 Jul 15;319(12):1759-1773. doi: 10.1016/j.yexcr.2013.03.019. Epub 2013 Apr 12. Exp Cell Res. 2013. PMID: 23588206 Free PMC article.
-
Total synthesis of complestatin: development of a Pd(0)-mediated indole annulation for macrocyclization.J Am Chem Soc. 2010 Jun 9;132(22):7776-83. doi: 10.1021/ja102304p. J Am Chem Soc. 2010. PMID: 20469945 Free PMC article.
Publication types
MeSH terms
Substances
LinkOut - more resources
Full Text Sources
