Back to Search
Start Over
Total synthesis of nafuredin B
- Source :
- Organic & Biomolecular Chemistry. 18:2346-2359
- Publication Year :
- 2020
- Publisher :
- Royal Society of Chemistry (RSC), 2020.
-
Abstract
- Total synthesis of marine secondary metabolite nafuredin B has been achieved for the first time using a convergent strategy. Sharpless epoxidation followed by acid catalyzed epoxide opening were adopted to install the tetrasubstituted hydroxy center, whereas the iterative Julia-Kocienski olefination, Wittig olefination and HWE olefination afforded the olefin bonds. Ring closing metathesis in the presence of a free tetrasubstituted hydroxy group provided the unsaturated δ-lactone moiety. This synthetic study provided unambiguous structural confirmation of the isolated nafuredin B.
- Subjects :
- Sharpless epoxidation
Olefin fiber
Molecular Structure
010405 organic chemistry
Stereochemistry
Organic Chemistry
Epoxide
Total synthesis
Alkenes
010402 general chemistry
01 natural sciences
Biochemistry
0104 chemical sciences
Lactones
chemistry.chemical_compound
Ring-closing metathesis
chemistry
Pyrones
Wittig reaction
Epoxy Compounds
Moiety
Molecule
Physical and Theoretical Chemistry
Subjects
Details
- ISSN :
- 14770539 and 14770520
- Volume :
- 18
- Database :
- OpenAIRE
- Journal :
- Organic & Biomolecular Chemistry
- Accession number :
- edsair.doi.dedup.....443dae82360c4536e6feed2df746246c