Download PDF
Synlett 1997; 1997(1): 109-110
DOI: 10.1055/s-1997-17829
letter
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

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
Further Information

Publication History

Publication Date:
22 March 2004 (online)

  PDF Download  Permissions and Reprints All articles of this category

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