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Synthesis 1995; 1995(9): 1066-1068
DOI: 10.1055/s-1995-4071
short paper
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Diastereoselective Synthesis of Merucathin: The Singlet Oxygen Ene Reaction (Schenck Reaction) as a Key Step Towards an E-Configured β-Amino Allylic Alcohol

Waldemar Adam, Hans-Günter Brünker*
  • *Institute of Organic Chemistry, University of Würzburg, Am Hubland, D-97074 Würzburg, Germany, Fax +49(931)8884756; E-mail Adam@vax.rz.uni-wuerzburg.d400.de
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Publication Date:
31 December 2000 (online)

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An enantio- and diastereoselective synthesis of the naturally occuring merucathin is reported. The singlet oxygen ene reaction of the bis-Boc-protected allylic amine 3, which was prepared from L-alanine, was employed as key step for this regio- and diastereoselective synthesis. The ene reaction is highly erythro-selective and the newly formed double bond in the allylic hydroperoxide 5 is exclusively E-configured. Reduction of the allylic hydroperoxide 5 and base-catalyzed deprotection provides a convenient and unprecedented synthesis of the optically active E-configured β-amino allylic alcohol merucathin from the corresponding acylated allylic amine 3.

singlet oxygen - ene reaction - stereoselective synthesis - merucathin

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