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  • Title: Absolute stereochemistry of citrinadins a and B from marine-derived fungus.
    Author: Mugishima T, Tsuda M, Kasai Y, Ishiyama H, Fukushi E, Kawabata J, Watanabe M, Akao K, Kobayashi J.
    Journal: J Org Chem; 2005 Nov 11; 70(23):9430-5. PubMed ID: 16268618.
    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).
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