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. 2014 Aug 15;16(16):4106-9.
doi: 10.1021/ol501805j. Epub 2014 Jul 29.

Stereoselective acylation of the E,E-vinylketene silyl N,O-acetal and its application to the synthesis of khafrefungin

Yuta Takahashi  1 , Maiko Otsuka, Mio Harachi, Yuki Mukaeda, Seijiro Hosokawa
Affiliations

Stereoselective acylation of the E,E-vinylketene silyl N,O-acetal and its application to the synthesis of khafrefungin

Yuta Takahashi et al. Org Lett. .

Abstract

Stereoselective acylation of the E,E-vinylketene silyl N,O-acetal possessing a chiral auxiliary has been achieved by using acid anhydrides and SnCl4. Acid anhydrides having alkyl chains gave the adducts in excellent stereoselectivity. The formal synthesis of khafrefungin has been accomplished by the methodology.

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