Synthetic Microbial Chemistry, XXVI. Absolute Configuration of (+)-Xanthocidin as Determined by the Synthesis of its Enantiomers of Known Stereochemistry

✍ Scribed by Mori, Kenji ;Horinaka, Akio ;Kido, Masaru

• Publisher: John Wiley and Sons
• Year: 1994
• Tongue: English
• Weight: 953 KB
• Volume: 1994
• Category: Article
• ISSN: 0947-3440
• DOI: 10.1002/jlac.199419940810

✦ Synopsis

Abstract

The absolute configuration of the antibiotic (+)‐xanthocidin (4,5‐dihydroxy‐5‐isopropyl‐4‐methyl‐2‐methylene‐3‐oxocyclopentane‐1‐carboxylicacid, 1) was shown to be 1__R__,4__S__,5__S__ by the synthesis of its enantiomers. Lipase AK (Amano) was used for the key resolution step, and the absolute configuration of the resolved intermediate (+)‐16 was determined by the X‐ray analysis of its (1__S__)‐camphanic ester (+)‐20. magnified image