Absolute stereochemistry of citrinadins A and B from marine-derived fungus

被引：189

作者：

Mugishima, T

Tsuda, M

Kasai, Y

Ishiyama, H

Fukushi, E

Kawabata, J

Watanabe, M

Akao, K

Kobayashi, J ^{[1
]}

机构：

[1] Hokkaido Univ, Grad Sch Pharmaceut Sci, Sapporo, Hokkaido 0600812, Japan

[2] Hokkaido Univ, Grad Sch Agr, Sapporo, Hokkaido 0608589, Japan

[3] JASCO Corp, Spectrometry Instrument Div, Hachioji, Tokyo 1920032, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 70卷 / 23期

关键词：

D O I：

10.1021/jo051499o

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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).

引用

页码：9430 / 9435

页数：6

共 33 条

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