Absolute stereochemistry of citrinadins A and B from marine-derived fungus
Absolute stereochemistry of citrinadins A and B from marine-derived fungus
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DOI：
10.1021/jo051499o
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发表时间：
2005-11-11
影响因子：
3.6
通讯作者：
Kobayashi, J
中科院分区：
文献类型：
--
作者：
Mugishima, T;Tsuda, M;Kobayashi, J
Citrinadin A (2) 是一种五环二氢吲哚酮生物碱，是从一种真菌柑橘青霉的培养液中分离出来的，该真菌是从海洋红藻中分离出来的。通过分析 1 的氯代醇衍生物 (3) 的 ROESY 光谱以及比较 1 和 2 的电子圆二色性 (ECD) 光谱与已知螺氧吲哚生物碱的电子圆二色性 (ECD) 光谱，阐明了 2 中五环核心及其新同源物柑橘丁 B (1) 的绝对立体化学。另一方面，通过比较 I 的振动圆二色性（VCD）光谱与模型化合物 2S-和 2R-2,3-环氧-3,3-二甲基-1-苯基丙-1-酮（分别为 4a 和 4b）的振动圆二色性（VCD）光谱，将带有环氧化物环的 C-21 处的绝对构型指定为 S。
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 I with those of model compounds 2S- and 2R-2,3-epoxy-3,3-dimethyl-1-phenylpropan-1-one (4a and 4b, respectively).