Stereochemical assignment of fusiccocadiene from NMR shielding constants and vibrational circular dichroism spectroscopy

Autor:	Frank Schulz, Michael Dirkmann, Christian Merten
Rok vydání:	2017
Předmět:	Models Molecular Magnetic Resonance Spectroscopy Infrared Stereochemistry Crystal structure 010402 general chemistry 01 natural sciences Catalysis Spectral line Analytical Chemistry Drug Discovery Spectroscopy Pharmacology 010405 organic chemistry Chemistry Chemical shift Circular Dichroism Organic Chemistry Absolute configuration Total synthesis Stereoisomerism 0104 chemical sciences Crystallography Vibrational circular dichroism Diterpenes
Zdroj:	Chirality. 29(8)
ISSN:	1520-636X
Popis:	The absolute configuration (AC) of the common precursor of the fusicoccane family of terpenoids, fusicocca-2,10(14)-diene (FCdiene), had only been deduced by a lengthy total synthesis, or indirectly from crystal structures of fusicoccin A. However, in particular the AC determinations based on downstream products of the terpene synthase intrinsically overlook potential epimerization reactions. In this contribution, we confirm the relative stereochemistry of FCdiene by comparison of experimental and predicted 13 C-NMR chemical shifts, and finally determine the absolute configuration from an analysis of its infrared and vibrational circular dichroism spectra.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::2bc90b8cdca9de0e3a4d2ae27c77a4b9 https://pubmed.ncbi.nlm.nih.gov/28560831 Zobrazit plný text záznamu Plný text ve formátu PDF Plný text ve formátu HTML
Nepřihlášeným uživatelům se plný text nezobrazuje	K zobrazení výsledku je třeba se přihlásit.