エキヌリンおよび関連化合物の合成研究(第6報) : Aurechinulinの構造および合成

概要

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A new alkaloid, named aurechinulin, was isolated from ether extract of freeze-dried mycelium of Aspergillus amstelodami IFO-6667. Elemental analysis and high-resolution mass spectral data showed the molecular formula of aurechinulin to be C_<43>H_<49>O_5N_3. This formula is equal to the sum of the molecular formulae of auroglaucin (2), C_<19>H_<22>O_3,and cryptoehinulin A (3), C_<24>H_<27>O_2N_3,both of which are metabolites of Aspergillus amstelodami. Alkaline hydrolysis of aurechinulin afforded 2-(1,1-dimethylallyl)-6-(3,3-dimethylallyl)-3-indolecarbaldehyde (4), an alkaline hydrolysis product of cryptoechinulin A (3). Analysis of proton magnetic resonance and carbon magnetic resonance (CMR) indicated the structure 1a for aurechinulin. Aurechinulin (1a) was synthesized by the Diels-Alder reaction of auroglaucin (2) and cryptoechinulin A (3) in 37% yield. A by-product (regio-or stereoisomer of 1a) was isolated in this Diels-Alder reaction in about 8% yield. Stereochemistry of 1a, except for C-3e, was determined as indicated in the structure of 1a.
公益社団法人日本薬学会の論文
1977-05-25