Enantioselective Synthesis of Nabscessin C

Chun Wei Yeh; Chia Chi Feng; Pei Lin Chen; Yi Jhen Jhou; Duen Ren Hou

doi:10.1021/acs.joc.3c01064

Enantioselective Synthesis of Nabscessin C

Chun Wei Yeh, Chia Chi Feng, Pei Lin Chen, Yi Jhen Jhou, Duen Ren Hou

Department of Chemistry

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

Abstract

Enantioselective synthesis of nabscessin C (1), an aminocyclitol amide with antimicrobial activity, is reported. Starting from myo-inositol, (+)-nabscessin C was synthesized in 12 isolation steps. Desymmetrization of 2-deoxygenated 4,6-dibenzylinositol was achieved using lipase from porcine pancreas (PPL), and the stereochemistry was established by X-ray crystallography. This method has the potential for synthesizing other cyclitol-derived compounds.

Original language	English
Pages (from-to)	13528-13534
Number of pages	7
Journal	Journal of Organic Chemistry
Volume	88
Issue number	19
DOIs	https://doi.org/10.1021/acs.joc.3c01064
State	Published - 6 Oct 2023

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10.1021/acs.joc.3c01064

不對稱合成肌醇衍生天然物與具鏡像選擇之麥可反應(2/2)
Hou, D.-R. (PI)
1/08/22 → 31/07/23
Project: Research
Asymmetric Synthesis Utilizing Oxazolidinone-Fused Aziridines
Hou, D.-R. (PI)
1/08/20 → 31/07/21
Project: Research

CCDC 2262453: Experimental Crystal Structure Determination
Yeh, C.-W. (Contributor), Feng, C.-C. (Contributor), Chen, P.-L. (Contributor), Jhou, Y.-J. (Contributor) & Hou, D.-R. (Contributor), Cambridge Crystallographic Data Centre, 2023
DOI: 10.5517/ccdc.csd.cc2fy8c1, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc2fy8c1&sid=DataCite
Dataset

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title = "Enantioselective Synthesis of Nabscessin C",

abstract = "Enantioselective synthesis of nabscessin C (1), an aminocyclitol amide with antimicrobial activity, is reported. Starting from myo-inositol, (+)-nabscessin C was synthesized in 12 isolation steps. Desymmetrization of 2-deoxygenated 4,6-dibenzylinositol was achieved using lipase from porcine pancreas (PPL), and the stereochemistry was established by X-ray crystallography. This method has the potential for synthesizing other cyclitol-derived compounds.",

author = "Yeh, {Chun Wei} and Feng, {Chia Chi} and Chen, {Pei Lin} and Jhou, {Yi Jhen} and Hou, {Duen Ren}",

note = "Publisher Copyright: {\textcopyright} 2023 American Chemical Society.",

year = "2023",

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doi = "10.1021/acs.joc.3c01064",

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T1 - Enantioselective Synthesis of Nabscessin C

AU - Yeh, Chun Wei

AU - Feng, Chia Chi

AU - Chen, Pei Lin

AU - Jhou, Yi Jhen

AU - Hou, Duen Ren

PY - 2023/10/6

Y1 - 2023/10/6

N2 - Enantioselective synthesis of nabscessin C (1), an aminocyclitol amide with antimicrobial activity, is reported. Starting from myo-inositol, (+)-nabscessin C was synthesized in 12 isolation steps. Desymmetrization of 2-deoxygenated 4,6-dibenzylinositol was achieved using lipase from porcine pancreas (PPL), and the stereochemistry was established by X-ray crystallography. This method has the potential for synthesizing other cyclitol-derived compounds.

AB - Enantioselective synthesis of nabscessin C (1), an aminocyclitol amide with antimicrobial activity, is reported. Starting from myo-inositol, (+)-nabscessin C was synthesized in 12 isolation steps. Desymmetrization of 2-deoxygenated 4,6-dibenzylinositol was achieved using lipase from porcine pancreas (PPL), and the stereochemistry was established by X-ray crystallography. This method has the potential for synthesizing other cyclitol-derived compounds.

UR - http://www.scopus.com/inward/record.url?scp=85172881451&partnerID=8YFLogxK

U2 - 10.1021/acs.joc.3c01064

DO - 10.1021/acs.joc.3c01064

M3 - 期刊論文

AN - SCOPUS:85172881451

SN - 0022-3263

VL - 88

SP - 13528

EP - 13534

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 19

ER -

Enantioselective Synthesis of Nabscessin C

Abstract

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Projects

不對稱合成肌醇衍生天然物與具鏡像選擇之麥可反應(2/2)

Asymmetric Synthesis Utilizing Oxazolidinone-Fused Aziridines

Datasets

CCDC 2262453: Experimental Crystal Structure Determination

Cite this