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Synlett 2001; 2001(7): 1105-1108
DOI: 10.1055/s-2001-15145
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Concise Synthesis of the C3-C14-Fragment of the Antitumor Agent Laulimalide. Application of Jacobsen's HKR Reaction

E. Kate Dorling* , Elisabeth Öhler, Andreas Mantoulidis, Johann Mulzer
  • *Institut für Organische Chemie der Universität Wien, Währinger Strasse 38, A-1090 Wien, Austria; E-mail: johann.mulzer@univie.ac.at
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Publication Date:
31 December 2001 (online)

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Bromide 3, which represents an appropriately functionalized C3-C14-fragment of the antitumor agent laulimalide (1) has been synthesized from (-)-citronellal (4) in an overall yield of ca. 17% (12 isolated intermediates). At a very early stage, the synthesis makes use of Jacobsen's HKR reaction to produce epoxide 8 in diastereomerically pure form.

antitumor agents - epoxides - Jacobsen's HKR reaction - Eschenmoser methylenation