Sceptrin : Enantioselective Synthesis of a Tetrasubstituted all-trans Cyclobutane Key Intermediate

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2017
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Dickschat, Jeroen S.
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European Journal of Organic Chemistry. Wiley-Blackwell - STM. 2017(31), pp. 4566-4571. ISSN 1434-2421. eISSN 1099-0682. Available under: doi: 10.1002/ejoc.201700882
Zusammenfassung

The asymmetric synthesis of both enantiomers of tetrasubstituted all-trans dimethyl 3,4-diacetylcyclobutane-1,2-dicarboxylate with high enantiomeric purity (>98 % ee) using a valine-derived chiral auxiliary in a diastereoselective photodimerization is reported. The absolute configuration was assigned by single-crystal X-ray diffraction analysis. Because this cyclobutane is a key intermediate in the total synthesis of (–)-sceptrin and ageliferin, our findings strengthen the recently revised absolute configurations of these pyrrole-imidazole alkaloids. An enantioselective synthesis of a tetrasubstituted all-trans cyclobutane, a key intermediate in the total synthesis of the pyrrole-imidazole alkaloid sceptrin, facilitated by a diastereoselective, valine-derived chiral-auxiliary-guided photodimerization, is reported.

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ISO 690BARRA, Lena, Jeroen S. DICKSCHAT, 2017. Sceptrin : Enantioselective Synthesis of a Tetrasubstituted all-trans Cyclobutane Key Intermediate. In: European Journal of Organic Chemistry. Wiley-Blackwell - STM. 2017(31), pp. 4566-4571. ISSN 1434-2421. eISSN 1099-0682. Available under: doi: 10.1002/ejoc.201700882
BibTex
@article{Barra2017Scept-57696,
  year={2017},
  doi={10.1002/ejoc.201700882},
  title={Sceptrin : Enantioselective Synthesis of a Tetrasubstituted all-trans Cyclobutane Key Intermediate},
  number={31},
  issn={1434-2421},
  journal={European Journal of Organic Chemistry},
  pages={4566--4571},
  author={Barra, Lena and Dickschat, Jeroen S.}
}
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