Total synthesis of khafrefungin using highly stereoselective vinylogous Mukaiyama aldol reaction.
[structure: see text] A convergent total synthesis of khafrefungin was accomplished on the basis of (1) the highly stereoselective TiCl4-mediated vinylogous Mukaiyama aldol reaction using vinylketene silyl N,O-acetal and (2) syn-selective aldol reaction of enal 5a and ethyl ketone 6 followed by anti-dehydration under Mitsunobu conditions.
Shirokawa
Shin-ichi
S
Faculty of Pharmaceutical Sciences, Tokyo University of Science (RIKADAI), 2641 Yamazaki, Noda-shi, Chiba 278-8510, Japan.
Shinoyama
Mariko
M
Ooi
Isao
I
Hosokawa
Seijiro
S
Nakazaki
Atsuo
A
Kobayashi
Susumu
S
D006017:Glycolipids / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
D006017:Glycolipids; C109747:khafrefungin