𝔖 Bobbio Scriptorium
✦   LIBER   ✦

Assignment of the stereochemistry of spiroxamine by two-dimensional NMR spectroscopy and stereoselective chemical synthesis

✍ Scribed by W. A. Etzel; W. Gau; W. Krämer; U. Stelzer; J. Weissmüller

Publisher
John Wiley and Sons
Year
1998
Tongue
English
Weight
278 KB
Volume
36
Category
Article
ISSN
0749-1581

No coin nor oath required. For personal study only.

✦ Synopsis

Spiroxamine is a new powdery mildew fungicide in cereals consisting of four biologically active isomers (two diastereomers, four enantiomers). The four isomers were separated by preparative high-performance liquid chromatography (HPLC) on a chiral stationary phase. At this stage it was not possible to assign their stereochemistry. Using stereoselective synthesis starting with the corresponding chirally pure glycerol derivates, the conÐguration at the asymmetric center, could be Ðxed. The resulting diastereomers were separated by preparative HPLC. Using COSY, HSQC and NOESY NMR spectroscopy it was possible to assign the conÐguration of the amino residue relative to the cyclohexyl ring. The 600 MHz 1H NMR spectra permitted a complete assignment of all proton signals. The stereochemical assignment is based on NOEs observed in the NOESY spectrum. 1998

📜 SIMILAR VOLUMES

Spectral assignment of poly(vinyl acetat
Spectral assignment of poly(vinyl acetate) by one and two dimensional NMR spectroscopy: Revisited
✍ Kaushik Dutta; Munia Mukherjee; A. S. Brar 📂 Article 📅 1999 🏛 John Wiley and Sons 🌐 English ⚖ 180 KB 👁 2 views

Poly(vinyl acetate) (PVA) prepared by photopolymerization was studied by a combination of one and two dimensional NMR spectroscopy. The 13 C{ 1 H} and 1 H NMR spectra of the homopolymer (PVA) were assigned to the configurational pentads (CH region) and tetrads (CH 2 region). These assignments were s

Conformational Studies and Stereochemica
Conformational Studies and Stereochemical Assignment of a Bicyclic Lactam-Containing Peptide Fragment by Two-Dimensional NMR Spectroscopy
✍ Jeff Kao; Wenhao Li; Kevin D. Moeller 📂 Article 📅 1997 🏛 John Wiley and Sons 🌐 English ⚖ 369 KB 👁 2 views

The stereochemistry and conformation of a key bicyclic lactam-based Leu-Pro building block and the conformation of the surrounding peptide fragment were assigned using a combination of 2D-NOE data and coupling constants from an NMR simulation. The work conÐrmed that the initial stereochemistry of th

Stereochemical and compositional assignm
Stereochemical and compositional assignments of trans-4-methacryloyloxyazobenzene–methyl methacrylate copolymers by one- and two-dimensional NMR spectroscopy
✍ A. S. Brar; M. Thiyagarajan 📂 Article 📅 1999 🏛 John Wiley and Sons 🌐 English ⚖ 278 KB 👁 2 views

The microstructure of trans-4-methacryloyloxyazobenzene-methyl methacrylate copolymers prepared by solution polymerization process using AIBN as initiator is analyzed by one-and two-dimensional spectroscopy. Sequence distribution was calculated from the 13 C( 1 H)-NMR spectra of the copolymers. Como

Total Assignment of the 1H and 13C NMR C
Total Assignment of the 1H and 13C NMR Chemical Shifts of Three Bisabolane Hydrocarbons by 2D-NMR Spectroscopy
✍ Lai-King Sy; Geoffrey D. Brown 📂 Article 📅 1997 🏛 John Wiley and Sons 🌐 English ⚖ 151 KB 👁 1 views

Three known bisabolane hydrocarbons, a-trans -bergamotene, sesquiphellandrene and zingiberene, were isolated from the aerial parts of Alpinia densibracteata . Their 1H and 13C NMR spectra were completely assigned by using a combination of 13C DEPT and 2D-NMR experiments (1H-1H COSY, single-bond 13C-