Absolute Stereochemistry of Citrinadins A and B from Marine-Derived Fungus
Citations Over TimeTop 10% of 2005 papers
Abstract
[Structure: see text]. Citrinadin A (2) is a pentacyclic indolinone alkaloid isolated from the cultured broth of a fungus, Penicillium citrinum, which was separated from a marine red alga. The absolute stereochemistry of the pentacyclic core in 2 and its new congener, citrinadin B (1), was elucidated by analysis of the ROESY spectrum for the chlorohydrin derivative (3) of 1 as well as comparison of the electronic circular dichroism (ECD) spectra for 1 and 2 with those of known spirooxiindole alkaloids. On the other hand, the absolute configuration at C-21 bearing an epoxide ring was assigned as S by comparison of the vibrational circular dichroism (VCD) spectra of 1 with those of model compounds 2S- and 2R-2,3-epoxy-3,3-dimethyl-1-phenylpropan-1-one (4a and 4b, respectively).
Related Papers
- → Absolute configuration determination of chiral molecules in the solution state using vibrational circular dichroism(2003)507 cited
- → Absolute configuration of diterpenoids from Jatropha dioica by vibrational circular dichroism(2016)14 cited
- → Determination of the Absolute Configuration of (−)-Mirtazapine by Vibrational Circular Dichroism(2002)26 cited
- → Vibrational Circular Dichroism for the Assignment of Absolute Configuration of Natural Products in Brazil(2021)6 cited
- → Absolute configuration assignment of (+)‐fluralaner using vibrational circular dichroism(2017)9 cited