Synthesis and absolute stereochemistry of a cruciferous phytoalexin, (-)-spirobrassinin

Authors
Monde, K Osawa, S Harada, N Takasugi, M Suchy, M Kutschy, P Dzurilla, M Balentova, E
Citation
K. Monde et al., Synthesis and absolute stereochemistry of a cruciferous phytoalexin, (-)-spirobrassinin, CHEM LETT, (8), 2000, pp. 886-887
Citations number
14
Categorie Soggetti
Chemistry
Journal title
CHEMISTRY LETTERS
ISSN journal
03667022 → ACNP
Issue
8
Year of publication
2000
Pages
886 - 887
Database
ISI
SICI code
0366-7022(20000805):8<886:SAASOA>2.0.ZU;2-6
Abstract
Synthetic (+/-)-spirobrassinin (1) was enantioresolved by a chiral auxiliar y method giving (+)-1 and natural (-)-1. The absolute configuration was una mbiguously determined by X-ray crystallography of a (1'S,4'R)-camphanoyl de rivative of (+)-1. Consequently, natural (-)-1 has an S configuration. Thei r CD spectra supported this result.