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Chromium-Mediated Asymmetric Synthesis of Both Enantiomers of Acetoxytubipofuran
- Source :
- Journal of the American Chemical Society, Vol. 125, No 19 (2003) pp. 5642-5643
- Publication Year :
- 2003
- Publisher :
- American Chemical Society (ACS), 2003.
-
Abstract
- Both enantiomers of acetoxytubipofuran were synthesized using enantioselective and diastereoselective dearomatization sequences starting from the benzaldehyde chromium tricarbonyl complex. Following aldol condensation, a sequence involving Pd-catalyzed allylic substitution was used in the synthesis of the (-)-enantiomer, whereas the (+)-enantiomer was reached via an Eschenmoser-Claisen rearrangement. Chiroptical data show that a revision of the previously assigned absolute configuration of the natural product is required.
- Subjects :
- Chromium
Allylic rearrangement
Terpenes
Stereochemistry
Absolute configuration
Enantioselective synthesis
chemistry.chemical_element
Stereoisomerism
General Chemistry
Biochemistry
Catalysis
Benzaldehyde
Cnidaria
chemistry.chemical_compound
Colloid and Surface Chemistry
chemistry
ddc:540
Animals
Organic synthesis
Aldol condensation
Enantiomer
Furans
Subjects
Details
- ISSN :
- 15205126 and 00027863
- Volume :
- 125
- Database :
- OpenAIRE
- Journal :
- Journal of the American Chemical Society
- Accession number :
- edsair.doi.dedup.....b08333e95a350cf9fc3d08956eb8fbda