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  • Title: Determination of the absolute configuration of Anisotome irregular diterpenes: application of CD and NMR methods.
    Author: Van Klink JW, Baek SH, Barlow AJ, Ishii H, Nakanishi K, Berova N, Perry NB, Weavers RT.
    Journal: Chirality; 2004 Oct; 16(8):549-58. PubMed ID: 15290691.
    Abstract:
    Several Anisotome diterpene derivatives were synthesized in an attempt to obtain a crystalline compound for X-ray analysis. Although we were unable to obtain a suitable crystal, the absolute configuration of the irregular diterpene skeleton was determined using two other techniques: a circular dichroism (CD) protocol based on a tetraarylporphyrin molecular tweezer that allowed prediction of the absolute stereochemistry on a microscale level, and a method employing differences in NMR shifts from derivatization of the naturally occurring acid 1 with enantiomers of a phenylglycine methyl ester (PGME) chiral anisotropic reagent. The excellent agreement between the CD and NMR methods led to the assignment of a 2S-absolute configuration for anisotomenoic acid 1.
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