Spiroketals via oxidative rearrangement of enol ethers
- PMID: 17164906
- DOI: 10.1039/b612992g
Spiroketals via oxidative rearrangement of enol ethers
Abstract
Oxidative rearrangement of cyclic enol ethers leads to alpha-alkoxyesters. In the presence of a neighboring spiroether, this approach provides a stereoselective access to spiroketals. A modified proposal for the biosynthesis of acutumine is presented.
Similar articles
-
Asymmetric synthesis of spiroketal, spiroether, and oxabicycle building blocks via stereoselective spiro- and bicycloannulation of 2-hydroxy dihydropyrans.Org Lett. 2008 Jul 3;10(13):2713-6. doi: 10.1021/ol800854s. Epub 2008 May 31. Org Lett. 2008. PMID: 18512930
-
Asymmetric total synthesis of pinnaic acid.Angew Chem Int Ed Engl. 2007;46(30):5746-9. doi: 10.1002/anie.200701581. Angew Chem Int Ed Engl. 2007. PMID: 17592606 No abstract available.
-
Synthesis of the core structure of acutumine.Org Lett. 2005 Mar 17;7(6):1089-92. doi: 10.1021/ol050020b. Org Lett. 2005. PMID: 15760146
-
Claisen rearrangement over the past nine decades.Chem Rev. 2004 Jun;104(6):2939-3002. doi: 10.1021/cr020703u. Chem Rev. 2004. PMID: 15186185 Review. No abstract available.
-
Organocatalytic oxidation. Asymmetric epoxidation of olefins catalyzed by chiral ketones and iminium salts.Chem Rev. 2008 Sep;108(9):3958-87. doi: 10.1021/cr068367v. Epub 2008 Jul 1. Chem Rev. 2008. PMID: 18590339 Review. No abstract available.
Cited by
-
Triple hybrids of steroids, spiroketals, and oligopeptides as new biomolecular chimeras.Org Lett. 2009 Jan 1;11(1):65-8. doi: 10.1021/ol802247m. Org Lett. 2009. PMID: 19067551 Free PMC article.
-
Enantioselective total synthesis of (-)-acutumine.J Org Chem. 2009 Dec 4;74(23):9082-93. doi: 10.1021/jo902006q. J Org Chem. 2009. PMID: 19904909 Free PMC article.
-
Synthetic Strategies toward Natural Products Containing Contiguous Stereogenic Quaternary Carbon Atoms.Angew Chem Int Ed Engl. 2016 Mar 18;55(13):4156-86. doi: 10.1002/anie.201507549. Epub 2016 Feb 2. Angew Chem Int Ed Engl. 2016. PMID: 26836448 Free PMC article. Review.
Publication types
MeSH terms
Substances
Grants and funding
LinkOut - more resources
Full Text Sources