Synthesis of Methyl l-Kijanosides by Regio-and Stereoselective Ring Opening of 2-Oxazolidinone-Fused Aziridines

Chi Yun Liu; Venkatachalam Angamuthu; Wei Chen Chen; Duen Ren Hou

doi:10.1021/acs.orglett.0c00443

Synthesis of Methyl l-Kijanosides by Regio-and Stereoselective Ring Opening of 2-Oxazolidinone-Fused Aziridines

Chi Yun Liu, Venkatachalam Angamuthu, Wei Chen Chen, Duen Ren Hou

化學學系

研究成果: 雜誌貢獻 › 期刊論文 › 同行評審

6 引文斯高帕斯（Scopus）

摘要

Kijanose is one of the most highly functionalized deoxysugars found in nature and a challenging synthetic target. We found that the ring opening of trisubstituted, 2-oxazolidinone-fused aziridines is regio-and stereoselective, and the azide adduct has the same stereochemistry as that of kijanose after converting the azido to a nitro group. Therefore, both α-and β-methyl l-kijanosides were prepared from ethyl l-lactate in 14% total yield.

原文	???core.languages.en_GB???
頁（從 - 到）	2246-2250
頁數	5
期刊	Organic Letters
卷	22
發行號	6
DOIs	https://doi.org/10.1021/acs.orglett.0c00443
出版狀態	已出版 - 20 3月 2020

存取文件

10.1021/acs.orglett.0c00443

天然物合成與氮環丙烷相關合成方法之發展(2/2)
Hou, D.-R. (PI)
1/08/19 → 31/07/20
研究計畫: Research
天然物合成與氮丙烷相關合成方法之發展
Hou, D.-R. (PI)
1/08/18 → 31/07/19
研究計畫: Research

CCDC 1977159: Experimental Crystal Structure Determination
Liu, C.-Y. (貢獻者), Angamuthu, V. (貢獻者), Chen, W.-C. (貢獻者) & Hou, D.-R. (貢獻者), The Cambridge Structural Database, 2020
DOI: 10.5517/ccdc.csd.cc24cdb8, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc24cdb8&sid=DataCite
資料集
CCDC 1954130: Experimental Crystal Structure Determination
Hou, D.-R. (貢獻者), The Cambridge Structural Database, 2019
DOI: 10.5517/ccdc.csd.cc23lfgm, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc23lfgm&sid=DataCite
資料集
CCDC 1570780: Experimental Crystal Structure Determination
Liu, C.-Y. (貢獻者), Angamuthu, V. (貢獻者), Chen, W.-C. (貢獻者) & Hou, D.-R. (貢獻者), The Cambridge Structural Database, 2020
DOI: 10.5517/ccdc.csd.cc1pqjb8, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc1pqjb8&sid=DataCite
資料集

引用此

@article{b69bf74b9fe1431c91522850f00e2239,

title = "Synthesis of Methyl l-Kijanosides by Regio-and Stereoselective Ring Opening of 2-Oxazolidinone-Fused Aziridines",

abstract = "Kijanose is one of the most highly functionalized deoxysugars found in nature and a challenging synthetic target. We found that the ring opening of trisubstituted, 2-oxazolidinone-fused aziridines is regio-and stereoselective, and the azide adduct has the same stereochemistry as that of kijanose after converting the azido to a nitro group. Therefore, both α-and β-methyl l-kijanosides were prepared from ethyl l-lactate in 14% total yield.",

author = "Liu, {Chi Yun} and Venkatachalam Angamuthu and Chen, {Wei Chen} and Hou, {Duen Ren}",

note = "Publisher Copyright: {\textcopyright} 2020 American Chemical Society.",

year = "2020",

month = mar,

day = "20",

doi = "10.1021/acs.orglett.0c00443",

language = "???core.languages.en_GB???",

volume = "22",

pages = "2246--2250",

journal = "Organic Letters",

issn = "1523-7060",

number = "6",

}

TY - JOUR

T1 - Synthesis of Methyl l-Kijanosides by Regio-and Stereoselective Ring Opening of 2-Oxazolidinone-Fused Aziridines

AU - Liu, Chi Yun

AU - Angamuthu, Venkatachalam

AU - Chen, Wei Chen

AU - Hou, Duen Ren

PY - 2020/3/20

Y1 - 2020/3/20

N2 - Kijanose is one of the most highly functionalized deoxysugars found in nature and a challenging synthetic target. We found that the ring opening of trisubstituted, 2-oxazolidinone-fused aziridines is regio-and stereoselective, and the azide adduct has the same stereochemistry as that of kijanose after converting the azido to a nitro group. Therefore, both α-and β-methyl l-kijanosides were prepared from ethyl l-lactate in 14% total yield.

AB - Kijanose is one of the most highly functionalized deoxysugars found in nature and a challenging synthetic target. We found that the ring opening of trisubstituted, 2-oxazolidinone-fused aziridines is regio-and stereoselective, and the azide adduct has the same stereochemistry as that of kijanose after converting the azido to a nitro group. Therefore, both α-and β-methyl l-kijanosides were prepared from ethyl l-lactate in 14% total yield.

UR - http://www.scopus.com/inward/record.url?scp=85081223999&partnerID=8YFLogxK

U2 - 10.1021/acs.orglett.0c00443

DO - 10.1021/acs.orglett.0c00443

M3 - 期刊論文

C2 - 32115955

AN - SCOPUS:85081223999

SN - 1523-7060

VL - 22

SP - 2246

EP - 2250

JO - Organic Letters

JF - Organic Letters

IS - 6

ER -

Synthesis of Methyl l-Kijanosides by Regio-and Stereoselective Ring Opening of 2-Oxazolidinone-Fused Aziridines

摘要

存取文件

指紋

專案

天然物合成與氮環丙烷相關合成方法之發展(2/2)

天然物合成與氮丙烷相關合成方法之發展

資料集

CCDC 1977159: Experimental Crystal Structure Determination

CCDC 1954130: Experimental Crystal Structure Determination

CCDC 1570780: Experimental Crystal Structure Determination

引用此