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Synlett 1997; 1997(1): 109-110
DOI: 10.1055/s-1997-17829
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Synthesis of Two Key Intermediates for Hennoxazole A

Zhenzhuang Cheng1 , Yasumasa Hamada2 , Takayuki Shioiri3
  • 1Faculty of Pharmaceutical Sciences, Nagoya City University, Tanabe-dori, Mizuho-ku, Nagoya 467, JAPAN
  • 2Faculty of Pharmaceutical Sciences, Chiba University, Yayoi-cho, Inage-ku, Chiba, JAPAN
  • 3Faculty of Pharmaceutical Sciences, Nagoya City University, Tanabe-dori, Mizuho-ku, Nagoya 467, JAPAN, Fax: +81-52-834-4172; E-mail: shioiri@phar.nagoya-cu.ac.jp
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Publication Date:
22 March 2004 (online)

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Two key intermediates used for the synthesis of hennoxazole A have been synthesized. The anti-β-protected hydroxyl epoxide 5 was prepared from (R)-(+)-malic acid by the stereoselective alkylation utilizing a chiral borane reagent as a key step. Construction of the dithiane substituted oxazole 6 was achieved by the coupling of L-(+)-lactic acid and L-serine methyl ester hydrochloride with diethyl phosphorocyanidate, followed by the construction of the oxazole ring.

stereoselective synthesis - hennoxazole A - anti-β-protected hydroxyl epoxide - dithiane substituted oxazole

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