Asymmetric total syntheses of cyclic nitrone-containing phlegmarine-type Lycopodium alkaloids, lycoposerramines-X and -Z
- PMID: 19908911
- DOI: 10.1021/jo9018182
Asymmetric total syntheses of cyclic nitrone-containing phlegmarine-type Lycopodium alkaloids, lycoposerramines-X and -Z
Abstract
The total syntheses of cyclic nitrone-containing phlegmarine-type Lycopodium alkaloids, lycoposerramines-X and -Z, were accomplished starting from (R)-3-methylcyclohexanone via Pd-catalyzed Suzuki-Miyaura coupling, Johnson-Claisen rearrangement, stereoselective hydroboration-oxidation reaction, and Mitsunobu reaction, thereby establishing the structures including the absolute configuration.
Similar articles
-
Asymmetric total syntheses of two phlegmarine-type alkaloids, lycoposerramines-V and -W, newly isolated from Lycopodium serratum.Org Lett. 2007 Sep 27;9(20):4069-72. doi: 10.1021/ol701871v. Epub 2007 Sep 8. Org Lett. 2007. PMID: 17824711
-
cis-Decahydroquinolines via asymmetric organocatalysis: application to the total synthesis of lycoposerramine Z.Org Lett. 2013 Jan 18;15(2):326-9. doi: 10.1021/ol303257y. Epub 2012 Dec 27. Org Lett. 2013. PMID: 23270499
-
MiPNO, a new chiral cyclic nitrone for enantioselective amino acid synthesis: the cycloaddition approach.Org Biomol Chem. 2010 Feb 21;8(4):864-72. doi: 10.1039/b918612c. Epub 2009 Dec 22. Org Biomol Chem. 2010. PMID: 20135045
-
Nitroxide-mediated radical processes.Chem Rec. 2005;5(1):27-35. doi: 10.1002/tcr.20033. Chem Rec. 2005. PMID: 15806563 Review.
-
Why are the terpenoid indole alkaloids of type I homochiral?Chirality. 2001 Aug;13(8):483-7. doi: 10.1002/chir.1065. Chirality. 2001. PMID: 11466772 Review.
Cited by
-
Total synthesis of the Lycopodium alkaloid serratezomine A using free radical-mediated vinyl amination to prepare a β-stannyl enamine linchpin.J Org Chem. 2013 Feb 1;78(3):822-43. doi: 10.1021/jo302333s. Epub 2012 Dec 28. J Org Chem. 2013. PMID: 23273261 Free PMC article.
-
Asymmetric synthesis of all the known phlegmarine alkaloids.J Org Chem. 2010 Dec 17;75(24):8564-70. doi: 10.1021/jo1019688. Epub 2010 Nov 15. J Org Chem. 2010. PMID: 21077636 Free PMC article.
-
Diastereo- and Enantioselective Iridium Catalyzed Coupling of Vinyl Aziridines with Alcohols: Site-Selective Modification of Unprotected Diols and Synthesis of Substituted Piperidines.J Am Chem Soc. 2015 Jun 24;137(24):7915-20. doi: 10.1021/jacs.5b04404. Epub 2015 Jun 15. J Am Chem Soc. 2015. PMID: 26074091 Free PMC article.
-
Mitsunobu reaction: assembling C-N bonds in chiral traditional Chinese medicine.RSC Adv. 2025 Feb 17;15(7):5167-5189. doi: 10.1039/d4ra08573f. eCollection 2025 Feb 13. RSC Adv. 2025. PMID: 39963451 Free PMC article. Review.
Publication types
MeSH terms
Substances
LinkOut - more resources
Full Text Sources