Biomimetically inspired asymmetric total synthesis of (+)-19-dehydroxyl arisandilactone A.
basic_science · Level V
Where this comes from
- Record sourced from PubMed, PMID 28139648.
- Also identified by DOI 10.1038/ncomms14233 and PMC identifier 5290315.
- Licence recorded as CC BY.
- The licence permits redistribution, so the abstract is shown in full and the full text is available from the publisher.
Abstract
Complex natural products are a proven and rich source of disease-modulating drugs and of efficient tools for the study of chemical biology and drug discovery. The architectures of complex natural products are generally considered to represent significant barriers to efficient chemical synthesis. Here we describe a concise and efficient asymmetric synthesis of 19-dehydroxyl arisandilactone A-which belongs to a family of architecturally unique, highly oxygenated nortriterpenoids isolated from the medicinal plant Schisandra arisanensis. This synthesis takes place by means of a homo-Michael reaction, a tandem retro-Michael/Michael reaction, and Cu-catalysed intramolecular cyclopropanation as key steps. The proposed mechanisms for the homo-Michael and tandem retro-Michael/Michael reactions are supported by density functional theory (DFT) calculation. The developed chemistry may find application for the synthesis of its other family members of Schisandraceae nortriterpenoids.
Medical subject headings
- Biomimetic Materials
- Chemistry Techniques, Synthetic
- Cyclopropanes
- Triterpenes