The first chemoenzymatic total synthesis of the phytotoxic nonenolide putaminoxin and its (5S,6E,9S)-diastereomer

被引：5
|
作者：
Dickmann, David [1 ,2 ]
Diekmann, Martin [2 ]
Holec, Claudia [2 ]
Pietruszka, Joerg [1 ,2 ]
机构：
[1] Forschungszentrum Julich, IBG 1 Biotechnol, D-52425 Julich, Germany
[2] Heinrich Heine Univ Dusseldorf, Forschungszentrum Julich, Inst Bioorgan Chem, Gebaude 15-13, D-52426 Julich, Germany
来源：
TETRAHEDRON | 2019年 / 75卷 / 06期
关键词：
Chemoenzymatic synthesis; Oxidative kinetic resolution; Alcohol dehydrogenase; Nonenolides; Putaminoxin; ASYMMETRIC TOTAL-SYNTHESIS; ORGANIC-SYNTHESIS;
D O I：
10.1016/j.tet.2018.12.027
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The limitations of an alcohol dehydrogenase regarding the oxidative kinetic resolution of homoallylic alcohol containing alkyl chains were investigated, leading to a valuable building block for the total synthesis of phytotoxic nonenolide putaminoxin. The enzymatic approach towards the enantioenriched homoallylic alcohol was compared to classical, nonenzymatic approaches using asymmetric reagent controlled allyl additions and the obtained building block was used for the total synthesis of putaminoxin and its (5S,6E,9S)-diastereomer. After the spectroscopic analysis of the synthesized compounds, discrepancies were observed to already published data of isolated and synthesized putaminoxin. Therefore, a systematic comparison of NMR data was carried out. The result underlines the necessity of total synthesis for the absolute assignment of configuration. (C) 2018 Elsevier Ltd. All rights reserved.
引用
收藏
页码：689 / 696
页数：8
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