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Synlett 1997; 1997(11): 1291-1293
DOI: 10.1055/s-1997-5796
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Synthetic Studies of Mniopetals. Intramolecular Diels-Alder Cycloaddition Approach for Access to a Key Tricyclic Driman-type Intermediate

Takeshi Murata, Makoto Ishikawa, Ryoko Nishimaki, Kin-ichi Tadano*
  • *Department of Applied Chemistry, Keio University, Hiyoshi, Kohoku-ku, Yokohama 223, Japan, Fax +81-45-563-0446; e-mail: tadano@applc.keio.ac.jp
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Publication History

Publication Date:
31 December 2000 (online)

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Intramolecular Diels-Alder cycloaddition of an enantiomerically pure butenolide tethering a diene unit, prepared from D-mannitol, provides two endo-cycloadducts in a ratio of 2.4:1. The major adduct possesses a tricyclic core structure with correct stereochemistry for total synthesis of novel driman-type sesquiterpenoid antibiotic mniopetals.

mniopetals - intramolecular Diels-Alder cycloaddition - tricyclic Driman-type compounds - endo-selectivity