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05:15
Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
6.9K
(2R,4S,5S)-5-Meth-oxy-4-methyl-3-oxohept-6-en-2-yl benzoate
Ann-Christin Schmidt1, Lyuba Iovkova1, Martin Hiersemann1
1Fakultät für Chemie und Chemische Biologie, Technische Universität Dortmund, Organische Chemie, 44227 Dortmund, Germany.
Iucrdata
|November 7, 2022
Summary
The synthesis of a C16H20O4 compound confirmed stereochemical configurations during fusaequisin A synthesis. X-ray crystallography verified the absolute configuration, excluding epimerization during methylation.
Area of Science:
- Organic Chemistry
- Crystallography
- Chemical Synthesis
Background:
- Fusaequisin A is a complex natural product requiring precise stereochemical control during synthesis.
- Understanding stereogenic center configurations is crucial for validating synthetic routes.
Purpose of the Study:
- To synthesize and characterize a key intermediate (C16H20O4) in the total synthesis of fusaequisin A.
- To confirm the stereochemical configurations of the intermediate's stereogenic centers.
- To rule out epimerization during the methylation step of the synthesis.
Main Methods:
- Total synthesis of the title compound C16H20O4.
- X-ray crystallography at 100 K to determine crystal structure.
- Anomalous dispersion for absolute configuration determination.
Main Results:
- The title compound was successfully synthesized.
- The crystal structure exhibits ortho-rhom-bic (P212121) symmetry.
- The absolute configuration was determined and found to be consistent with the starting allylic alcohol.
Conclusions:
- The synthesized compound's absolute configuration was confirmed.
- The methylation process did not lead to epimerization of the stereogenic centers.
- This work validates a key step in the total synthesis of fusaequisin A.
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