Synthesis of (3S)-Hydroxyandrosta-5,7-diene-17-ones via Intramolecular Cobalt-Mediated [2+2+2] Cycloaddition

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2006
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Richter, Norbert
Kalogerakis, Aris
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Synlett. 2006, 2006(6), pp. 905-908. ISSN 0936-5214. eISSN 1437-2096. Available under: doi: 10.1055/s-2006-939064
Zusammenfassung

A new method for the synthesis of lumisterin-type steroids following the D→ABCD approach is reported. A key step is the cobalt-induced cyclization of a cyclopentanoid enediyne, which was prepared via thioalkylation of the zinc enolate of a 2,3-substituted cyclopentanone with α-chlorosulfides.

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540 Chemie
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cobalt, cycloaddition, cyclopentanones, steroids, vitamins
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ISO 690GROTH, Ulrich, Norbert RICHTER, Aris KALOGERAKIS, 2006. Synthesis of (3S)-Hydroxyandrosta-5,7-diene-17-ones via Intramolecular Cobalt-Mediated [2+2+2] Cycloaddition. In: Synlett. 2006, 2006(6), pp. 905-908. ISSN 0936-5214. eISSN 1437-2096. Available under: doi: 10.1055/s-2006-939064
BibTex
@article{Groth2006Synth-10068,
  year={2006},
  doi={10.1055/s-2006-939064},
  title={Synthesis of (3S)-Hydroxyandrosta-5,7-diene-17-ones via Intramolecular Cobalt-Mediated [2+2+2] Cycloaddition},
  number={6},
  volume={2006},
  issn={0936-5214},
  journal={Synlett},
  pages={905--908},
  author={Groth, Ulrich and Richter, Norbert and Kalogerakis, Aris}
}
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