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Communication | Special issue | Vol 47, No. 1, 1998, pp.73-76
Published online, 1st January, 1970
DOI: 10.3987/COM-97-S(N)7
A Synthesis of a C1-C7 Building Block for the Enantiomer of Hennoxazole A Utilizing a Regioselective Ring Opening of a Cyclic Acetal

Takayuki Shioiri,* Nigel McFarlane, and Yasumasa Hamada

*Faculty of Pharmaceutical Sciences, Nagoya City University, Tanabe-dori, Mizuho-ku, Nagoya 467-8603, Japan

Abstract

AC1-C7 building block (4) for the enantiomer of hennoxazole A(1), an antivirus and analgesic active marine natural product, was efficiently synthesized from (S)-malic acid utilizing the following key steps: (1) the stereoselective construction of an anti-1,3-diol, (2) the regioselective ring opening of a cyclic acetal, and (3) the oxidative transformation of the olefin into the ketal of the methyl ketone in a one-pot process.