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Synlett 1991; 1991(5): 343-344
DOI: 10.1055/s-1991-34738
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Formal Total Synthesis of Clausenamide

Takayuki Yakura* , Yukiko Matsumura, Masazumi Ikeda
  • *Kyoto Pharmaceutical University, Misasagi, Yamashina, Kyoto 607, Japan
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Publication Date:
07 March 2002 (online)

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Ruthenium tetroxide oxidation of trans-5-substituted 4-acylaminocyclohexenes 2 followed by esterification gave N-protected cis-4-substituted 5-(methoxycarbonylmethyl)-2-pyrrolidones 4. The resulting pyrrolidone 4a (N-Boc-4-phenyl) was converted into the key intermediate 8 (cis-5-formal-1-methyl-4-phenyl-2-pyrrolidinone), thus achieving the formal total synthesis of clausenamide [3-hydroxy-5-(α-hydroxybenzyl)-1-methyl-4-phenyl-2-pyrrolidinone].