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Total Synthesis of (+)‐Sarcophytin
- Source :
- Angewandte Chemie. 130:831-834
- Publication Year :
- 2017
- Publisher :
- Wiley, 2017.
-
Abstract
- A total synthesis of the cembranoid (+)-sarcophytin is presented, featuring a Diels-Alder cycloaddition of an enone as the dienophile with an ester-derived dienoate. The study highlights a peculiar geometric preference for the Z dienoate to furnish the cycloadduct. The endgame involves a reaction cascade, including lactone opening, alcohol oxidation, and ketone epimerization to complete an efficient synthesis. A salient feature of the synthesis is the resulting reassignment of the absolute configuration, which corrects the previously reported nominal structure.
- Subjects :
- chemistry.chemical_classification
Ketone
Stereochemistry
010405 organic chemistry
Absolute configuration
Total synthesis
General Chemistry
General Medicine
010402 general chemistry
01 natural sciences
Catalysis
Cycloaddition
0104 chemical sciences
chemistry.chemical_compound
chemistry
Alcohol oxidation
Enone
Lactone
Diels–Alder reaction
Subjects
Details
- ISSN :
- 15213757 and 00448249
- Volume :
- 130
- Database :
- OpenAIRE
- Journal :
- Angewandte Chemie
- Accession number :
- edsair.doi.dedup.....454fd8521fb5afb408ca740ac8230a19
- Full Text :
- https://doi.org/10.1002/ange.201711372