Structure Confirmation of Dechlorotrichotoxin A through Stereoselective Total Synthesis

IF 3.3 2区 生物学 Q2 CHEMISTRY, MEDICINAL
Dawon Bae, Joo-Won Nam, Hyojin Park, Prakash Chaudhary, Jung-Ae Kim, Hyunji Lee* and Byeong-Seon Jeong*, 
{"title":"Structure Confirmation of Dechlorotrichotoxin A through Stereoselective Total Synthesis","authors":"Dawon Bae,&nbsp;Joo-Won Nam,&nbsp;Hyojin Park,&nbsp;Prakash Chaudhary,&nbsp;Jung-Ae Kim,&nbsp;Hyunji Lee* and Byeong-Seon Jeong*,&nbsp;","doi":"10.1021/acs.jnatprod.3c00629","DOIUrl":null,"url":null,"abstract":"<p >The stereoselective total synthesis of dechlorotrichotoxin A, alongside the synthesis of a 1:1 10<i>E</i>/<i>Z</i> mixture of trichotoxin A, was successfully achieved, commencing from the natural monoterpenoid (−)-citronellal. Key steps in the synthesis involved introducing three alkenes and establishing a stereogenic secondary alcohol center. These transformations were accomplished through olefin cross-metathesis, Tebbe olefination, and enantioselective allylation using a chiral phosphoric acid. A comparison of the spectroscopic data between the synthetic dechlorotrichotoxin A and the reported spectra confirmed that the polyketide isolated from a <i>Smenospongia</i> species corresponds to trichotoxin A rather than dechlorotrichotoxin A.</p>","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":"86 11","pages":"2585–2591"},"PeriodicalIF":3.3000,"publicationDate":"2023-10-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Natural Products ","FirstCategoryId":"99","ListUrlMain":"https://pubs.acs.org/doi/10.1021/acs.jnatprod.3c00629","RegionNum":2,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, MEDICINAL","Score":null,"Total":0}
引用次数: 0

Abstract

The stereoselective total synthesis of dechlorotrichotoxin A, alongside the synthesis of a 1:1 10E/Z mixture of trichotoxin A, was successfully achieved, commencing from the natural monoterpenoid (−)-citronellal. Key steps in the synthesis involved introducing three alkenes and establishing a stereogenic secondary alcohol center. These transformations were accomplished through olefin cross-metathesis, Tebbe olefination, and enantioselective allylation using a chiral phosphoric acid. A comparison of the spectroscopic data between the synthetic dechlorotrichotoxin A and the reported spectra confirmed that the polyketide isolated from a Smenospongia species corresponds to trichotoxin A rather than dechlorotrichotoxin A.

Abstract Image

立体选择性全合成法确认脱氯毛毒素A的结构。
从天然单萜类(-)-香茅醛开始,成功地实现了脱氯毛毒素A的立体选择性全合成,以及毛毒素A 1:1 10E/Z混合物的合成。合成的关键步骤包括引入三种烯烃并建立立体生成仲醇中心。这些转化是通过使用手性磷酸的烯烃交叉复分解、Tebbe烯烃化和对映选择性烯丙基化来实现的。合成的脱氯毛毒素A与报道的光谱之间的光谱数据的比较证实,从Smenospongia物种分离的聚酮对应于毛毒素A而不是脱氯毛毒A。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
求助全文
约1分钟内获得全文 求助全文
来源期刊
CiteScore
9.10
自引率
5.90%
发文量
294
审稿时长
2.3 months
期刊介绍: The Journal of Natural Products invites and publishes papers that make substantial and scholarly contributions to the area of natural products research. Contributions may relate to the chemistry and/or biochemistry of naturally occurring compounds or the biology of living systems from which they are obtained. Specifically, there may be articles that describe secondary metabolites of microorganisms, including antibiotics and mycotoxins; physiologically active compounds from terrestrial and marine plants and animals; biochemical studies, including biosynthesis and microbiological transformations; fermentation and plant tissue culture; the isolation, structure elucidation, and chemical synthesis of novel compounds from nature; and the pharmacology of compounds of natural origin. When new compounds are reported, manuscripts describing their biological activity are much preferred. Specifically, there may be articles that describe secondary metabolites of microorganisms, including antibiotics and mycotoxins; physiologically active compounds from terrestrial and marine plants and animals; biochemical studies, including biosynthesis and microbiological transformations; fermentation and plant tissue culture; the isolation, structure elucidation, and chemical synthesis of novel compounds from nature; and the pharmacology of compounds of natural origin.
×
引用
GB/T 7714-2015
复制
MLA
复制
APA
复制
导出至
BibTeX EndNote RefMan NoteFirst NoteExpress
×
提示
您的信息不完整,为了账户安全,请先补充。
现在去补充
×
提示
您因"违规操作"
具体请查看互助需知
我知道了
×
提示
确定
请完成安全验证×
copy
已复制链接
快去分享给好友吧!
我知道了
右上角分享
点击右上角分享
0
联系我们:info@booksci.cn Book学术提供免费学术资源搜索服务,方便国内外学者检索中英文文献。致力于提供最便捷和优质的服务体验。 Copyright © 2023 布克学术 All rights reserved.
京ICP备2023020795号-1
ghs 京公网安备 11010802042870号
Book学术文献互助
Book学术文献互助群
群 号:481959085
Book学术官方微信