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Synthesis 2009(17): 2983-2991  
DOI: 10.1055/s-0029-1216927
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Formal Synthesis of Salinosporamide A Starting from d-Glucose

Takayuki Momose, Yuji Kaiya, Jun-ichi Hasegawa, Takaaki Sato, Noritaka Chida*
Department of Applied Chemistry, Faculty of Science and Technology, Keio University, Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan
Fax: +81(45)5661551; e-Mail: chida@applc.keio.ac.jp;
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Publikationsverlauf

Received 19 July 2009
Publikationsdatum:
07. August 2009 (online)

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Abstract

A formal synthesis of salinosporamide A is described. The tertiary alcohol function in salinosporamide A was stereoselectively generated via the substrate control by the reaction of a cyclic ketone derived from d-glucose with Me3Al, and subsequent Overman rearrangement of an allylic trichloroacetimidate effectively constructed the tetrasubstituted carbon with nitrogen. Formation of γ-lactam, followed by the introduction of a cyclohexenyl unit furnished the Corey’s intermediate of salinosporamide A.

Key words

stereoselective synthesis - carbohydrates - chiral pool - rearrangements - pericyclic reactions

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