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

Yuta Takahashi; Maiko Otsuka; Mio Harachi; Yuki Mukaeda; Seijiro Hosokawa

doi:10.1021/ol501805j

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

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

Authors

Yuta Takahashi¹, Maiko Otsuka, Mio Harachi, Yuki Mukaeda, Seijiro Hosokawa

Affiliation

¹ Department of Applied Chemistry, Faculty of Science and Engineering, Waseda University , 3-4-1 Ohkubo, Shinjuku-ku, Tokyo 169-8555, Japan.

PMID: 25072267
DOI: 10.1021/ol501805j

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Acetals / chemistry*
Acylation
Anhydrides / chemistry
Catalysis
Glycolipids / chemical synthesis*
Glycolipids / chemistry
Molecular Structure
Silanes / chemistry*

Substances

Acetals
Anhydrides
Glycolipids
Silanes
khafrefungin