74 ねじれたπ電子共役系の円二色性と絶対構造 : 天然物への応用

概要

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The π-electron SCF-CI-dipole velocity molecular orbital method for the calculation of CD spectra is a quite useful tool for determination of the absolute stereochemistry of natural products with a distorted π-electron chromophore. By the calculation of CD curve, we have determined the absolute stereochemistry of (+)-1,8a-dihydro-3,8-dimethylazulene isolated from the cell culture of the liverwort Calypogeia granulata Inoue as a labile biosynthetic intermediate for 1,4-dimethylazulene, to be (8aS)-(+). The conclusion has been experimentally proven by the synthesis of pertinent chiral model compounds. The absolute configuration of the synthetic chiral troponoid spiro compounds has also been determined as shown by applying the present method. Finally, the absolute stereostructure of halenaquinol, pentacyclic hydroquinone from the Okinawan marine sponge Xesospongia sapra, has been determined by the calculation of the CD curve of the naphthalene-diene derivative.
天然有機化合物討論会の論文
1985-09-07