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

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

3 Scopus citations

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.

Original language	English
Pages (from-to)	13153-13159
Number of pages	7
Journal	Journal of Organic Chemistry
Volume	85
Issue number	20
DOIs	https://doi.org/10.1021/acs.joc.0c01839
State	Published - 16 Oct 2020

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10.1021/acs.joc.0c01839

Synthesis of Natural Products and Development of Aziridine-Related Methodology( II )
Hou, D.-R. (PI)
1/08/19 → 31/07/20
Project: Research
Synthesis of Natural Products and Development of Aziridine-Related Methodology(I)
Hou, D.-R. (PI)
1/08/18 → 31/07/19
Project: Research

Cite this

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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.",

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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.

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M3 - 期刊論文

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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

Abstract

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Projects

Synthesis of Natural Products and Development of Aziridine-Related Methodology( II )

Synthesis of Natural Products and Development of Aziridine-Related Methodology(I)

Cite this