Application of the cd homoallylic benzoate method as a chiroptical tool for determination of absolute configuration
โ Scribed by Shunichi Manabe; Nobuyasu Enoki; Chikao Nishino
- Book ID
- 104229117
- Publisher
- Elsevier Science
- Year
- 1985
- Tongue
- French
- Weight
- 306 KB
- Volume
- 26
- Category
- Article
- ISSN
- 0040-4039
No coin nor oath required. For personal study only.
โฆ Synopsis
After the conformation I was clarified to 5a,lOa-cis-solidagolactones by lH NMR measurement with Eu(dpm)3 and chemical transformations, the CD homoallylic benzoate chirality method was applied to the homoallylic alcohol system of solidagolactone IV (la) for a chiroptical determination of the absolute configuration. The result agreed with t.6 absolute configuration elucidated by X-ray analysis, indicating the usefulness of the CD method. The allylic benzoate chirality method, a CD exciton chirality method', has been successfully applied for determining absolute configurations of allylic alcohols2. Naya et 02.~ determined the absolute structure of the insect sesterterpene, 5-hydroxyfloridenol, in which the 5-OH functioned as both allylic and homoallylic alcohols. They observed, therefore, a positive Cotton effect composed of both allylic and homoallylic benzoate chiralities in the CD of 5-p-bromobenzoate derivative of the sesterterpene. This suggested that the homoallylic benzoate chirality may be arised from the same chiral exciton coupling mechanismas in thecaseof allylic benzoate chirality. In the present case, a 5a,lOcc-cis-solidagolactone, solidagolactone IV (la) (clerodane diterpene) which was isolated from SoZidago aZtis.stia L. as a piscicidal
๐ SIMILAR VOLUMES
The absolute configuration of beta-hydroxy-alpha-amino acids was studied by CD exciton chirality method using 7-diethylaminocoumarin-3-carboxylate as a red-shifted chromophore. The CD spectra of bischromophoric derivatives of (S)-serine and (2S,3R)-threonine methyl esters (2 and 7) were compared wit
gave good optical yields in the kinetic resolution of aryl-t-butylacetic anhydride, establishing the abso-