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立体化学研究普那澳酸,一种来自东印度洋-太平洋蓝细菌 Pseudanabaena sp. 的烯酸脂肪酸。

Stereochemical Study of Puna'auic Acid, an Allenic Fatty Acid from the Eastern Indo-Pacific Cyanobacterium Pseudanabaena sp.

机构信息

C-TAC, COMETE UMR 8638 CNRS , Université Paris Descartes , 4 avenue de l'observatoire , 75006 Paris , France.

Marine Biodiscovery Laboratory, School of Chemistry and Ryan Institute , National University of Ireland Galway (NUI Galway) , University Road , H91TK33 Galway , Ireland.

出版信息

Org Lett. 2018 Apr 20;20(8):2311-2314. doi: 10.1021/acs.orglett.8b00654. Epub 2018 Mar 29.

DOI:10.1021/acs.orglett.8b00654
PMID:29595272
Abstract

The isolation and structure elucidation of puna'auic acid, an allenic fatty acid isolated from a marine cyanobacterium, is described. All configurations were first assessed through molecular modeling of NMR and ECD spectra and then confirmed through a straightforward enantioselective total synthesis of puna'auic acid featuring a key reductive opening of a propargylic epoxide.

摘要

本文描述了一种从海洋蓝细菌中分离得到的烯丙基脂肪酸——普那乌酸的分离和结构解析。所有构型均首先通过 NMR 和 ECD 光谱的分子建模进行评估,然后通过普那乌酸的关键还原开环的对映选择性全合成进行确认,该反应具有炔丙基环氧化物。

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