Synthesis of Two Key Intermediates for Hennoxazole A

Zhenzhuang Cheng; Yasumasa Hamada; Takayuki Shioiri

doi:10.1055/s-1997-17829

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

Abstract

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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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