Asymmetric Synthesis of Nabscessin A from Inositol and d -Camphor

Hsin Ying Wu; Wei Yi Wang; Chia Chi Feng; Duen Ren Hou

doi:10.1021/acs.joc.0c01839

Asymmetric Synthesis of Nabscessin A from Inositol and d -Camphor

Hsin Ying Wu, Wei Yi Wang, Chia Chi Feng, Duen Ren Hou

化學學系

研究成果: 雜誌貢獻 › 期刊論文 › 同行評審

3 引文斯高帕斯（Scopus）

摘要

An enantiomer of nabscessin A (1), an aminocyclitol amide with antimicrobial activity, was synthesized from myo-inositol and dimethyl d-camphor acetal in 14 steps. Formal synthesis of natural nabscessin A was also achieved through the new approach to access both enantiomers of 4,5-di-O-benzyl-myo-inositol, derived from the same set of starting materials. This synthesis features utilizations of the existing framework of myo-inositol and a regioselective esterification.

原文	???core.languages.en_GB???
頁（從 - 到）	13153-13159
頁數	7
期刊	Journal of Organic Chemistry
卷	85
發行號	20
DOIs	https://doi.org/10.1021/acs.joc.0c01839
出版狀態	已出版 - 16 10月 2020

存取文件

10.1021/acs.joc.0c01839

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

引用此

@article{f33106dea9874b71af70541e7e2889a2,

title = "Asymmetric Synthesis of Nabscessin A from Inositol and d -Camphor",

abstract = "An enantiomer of nabscessin A (1), an aminocyclitol amide with antimicrobial activity, was synthesized from myo-inositol and dimethyl d-camphor acetal in 14 steps. Formal synthesis of natural nabscessin A was also achieved through the new approach to access both enantiomers of 4,5-di-O-benzyl-myo-inositol, derived from the same set of starting materials. This synthesis features utilizations of the existing framework of myo-inositol and a regioselective esterification.",

author = "Wu, {Hsin Ying} and Wang, {Wei Yi} and Feng, {Chia Chi} and Hou, {Duen Ren}",

year = "2020",

month = oct,

day = "16",

doi = "10.1021/acs.joc.0c01839",

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

volume = "85",

pages = "13153--13159",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

number = "20",

}

TY - JOUR

T1 - Asymmetric Synthesis of Nabscessin A from Inositol and d -Camphor

AU - Wu, Hsin Ying

AU - Wang, Wei Yi

AU - Feng, Chia Chi

AU - Hou, Duen Ren

PY - 2020/10/16

Y1 - 2020/10/16

N2 - An enantiomer of nabscessin A (1), an aminocyclitol amide with antimicrobial activity, was synthesized from myo-inositol and dimethyl d-camphor acetal in 14 steps. Formal synthesis of natural nabscessin A was also achieved through the new approach to access both enantiomers of 4,5-di-O-benzyl-myo-inositol, derived from the same set of starting materials. This synthesis features utilizations of the existing framework of myo-inositol and a regioselective esterification.

AB - An enantiomer of nabscessin A (1), an aminocyclitol amide with antimicrobial activity, was synthesized from myo-inositol and dimethyl d-camphor acetal in 14 steps. Formal synthesis of natural nabscessin A was also achieved through the new approach to access both enantiomers of 4,5-di-O-benzyl-myo-inositol, derived from the same set of starting materials. This synthesis features utilizations of the existing framework of myo-inositol and a regioselective esterification.

UR - http://www.scopus.com/inward/record.url?scp=85096507722&partnerID=8YFLogxK

U2 - 10.1021/acs.joc.0c01839

DO - 10.1021/acs.joc.0c01839

M3 - 期刊論文

AN - SCOPUS:85096507722

SN - 0022-3263

VL - 85

SP - 13153

EP - 13159

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 20

ER -

Asymmetric Synthesis of Nabscessin A from Inositol and d -Camphor

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

引用此