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Synlett 2001; 2001(1): 0090-0092
DOI: 10.1055/s-2001-9714
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Synthetic Studies towards Mniopetals (III). Solid Phase Organic Synthesis of a Key Intermediate for Combinatorial Synthesis of Mniopetals, Kuehneromycins and Marasmanes

Ulrich Reiser* , Johann Jauch
  • *Institut für Organische Chemie und Biochemie, Technische Universität München, Lichtenbergstr. 4, 85747 Garching, Germany; Fax (0)89-289 13329; E-mail: Johann.Jauch§ch.tum.de
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Publication Date:
31 December 2001 (online)

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The Solid Phase Organic Synthesis (SPOS) of an advanced building block for mniopetals, kuehneromycins, marasmanes and libraries thereof is presented. The synthesis is a sequence of a Michaelis-Arbuzov reaction, Horner-Wadsworth-Emmons reaction, hydroboration/oxidation, IBX oxidation, a new variant of the Baylis-Hillman reaction and a domino Dess-Martin oxidation/Intramolecular Diels-Alder reaction.

solid phase synthesis - Michaelis-Arbuzov reaction - Horner-Wadsworth-Emmons reaction - oxidation - intramolecular Diels-Alder reaction