title: Stereoselective acylation of the E,E-vinylketene silyl N,O-acetal and its application to the synthesis of khafrefungin.
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.
authors: Department of Applied Chemistry, Faculty of Science and Engineering, Waseda University , 3-4-1 Ohkubo, Shinjuku-ku, Tokyo 169-8555, Japan.
authors: Yuta
authors: Y
authors: Takahashi
authors: Maiko
authors: M
authors: Otsuka
authors: Mio
authors: M
authors: Harachi
authors: Yuki
authors: Y
authors: Mukaeda
authors: Seijiro
authors: S
authors: Hosokawa
mesh_terms: D000080:Acetals / Q000737:chemistry*; D000215:Acylation; D000812:Anhydrides / Q000737:chemistry; D002384:Catalysis; D006017:Glycolipids / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D012821:Silanes / Q000737:chemistry*
chemical_list: D000080:Acetals; D000812:Anhydrides; D006017:Glycolipids; D012821:Silanes; C109747:khafrefungin