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Synthesis 1993; 1993(6): 615-622
DOI: 10.1055/s-1993-25913
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Practical Asymmetric Synthesis of Hastanecine and Dihydroxyheliotridane by a Claisen Rearrangement/Amine-Epoxide-Opening Sequence

Johann Mulzer* , Michael Scharp
  • *Institut für Organische Chemie der Freien Universität Berlin, Takustraße 3, D-1000 Berlin 33, Germany
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Publication History

Publication Date:
17 September 2002 (online)

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A practical 13-step synthesis of the title compounds suitable for the gram scale has been developed. Key steps are Sharpless resolution, Claisen rearrangement, epoxidation and intramolecular SN2 ring closure to form the pyrrolizidine system.