Asymmetric Synthesis of (+)-(1R,2S)-allo-Coronamic Acid

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1992
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Halfbrodt, Wolfgang
Schöllkopf, Ulrich
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Liebigs Annalen der Chemie. 1992, 1992(4), pp. 351-355. ISSN 0170-2041. eISSN 1099-0690. Available under: doi: 10.1002/jlac.199219920162
Zusammenfassung

allo-Coronamic acid (1) was synthesized in five steps enantiomerically and diastereomerically virtually pure by starting from the bislactim ethers of cyclo(-L-Val-Gly-) (3a) or cyclo- (-L-tert-Leu-Gly-) (3b) in an overall yield of 31%. The key step of this synthesis is the intramolecular alkylation of the lithium azaenolate derived from the allylic chloride 4.

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Fachgebiet (DDC)
540 Chemie
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Amino acids, Cyclopropanation, diastereoselective, Bislactim ether method
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ISO 690GROTH, Ulrich, Wolfgang HALFBRODT, Ulrich SCHÖLLKOPF, 1992. Asymmetric Synthesis of (+)-(1R,2S)-allo-Coronamic Acid. In: Liebigs Annalen der Chemie. 1992, 1992(4), pp. 351-355. ISSN 0170-2041. eISSN 1099-0690. Available under: doi: 10.1002/jlac.199219920162
BibTex
@article{Groth1992Asymm-9670,
  year={1992},
  doi={10.1002/jlac.199219920162},
  title={Asymmetric Synthesis of (+)-(1R,2S)-allo-Coronamic Acid},
  number={4},
  volume={1992},
  issn={0170-2041},
  journal={Liebigs Annalen der Chemie},
  pages={351--355},
  author={Groth, Ulrich and Halfbrodt, Wolfgang and Schöllkopf, Ulrich}
}
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