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Synlett 1995; 1995(9): 909-911
DOI: 10.1055/s-1995-5142
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Intramolecular Diels-Alder Route to cis-Octalins: Facile Construction of the Alicyclic Skeletons of Acyltetramic Acid Antibiotics

Toru Hasegawa, Masaru Kido, Masahiko Bando, Takeshi Kitahara*
  • *Department of Applied Biological Chemistry, Division of Agriculture and Agricultural Life Science, The University of Tokyo, 1-1-1 Yayoi, Bunkyo-ku, Tokyo 113, Japan
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Publication Date:
31 December 2000 (online)

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γ-Substituted α,β-unsaturated δ-lactone 14b was thermally cyclized via intramolecular Diels-Alder reaction to afford tricyclic systems in sealed tube. Interestingly, the cis-octalin 16 predominated probably because of the presence of lactone ring. The cis-isomer must be a good candidate convertible to acyltetramic acid antibiotics.

Intramolecular Diels-Alder Reaction - Acyltetramic Acid Antibiotics - cis-Octalin