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Synthetic Microbial Chemistry, XXVI. Absolute Configuration of (+)‐Xanthocidin as Determined by the Synthesis of its Enantiomers of Known Stereochemistry
Author(s) -
Mori Kenji,
Horinaka Akio,
Kido Masaru
Publication year - 1994
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.199419940810
Subject(s) - chemistry , enantiomer , absolute configuration , stereochemistry , absolute (philosophy) , organic chemistry , computational chemistry , epistemology , philosophy
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 .