Syntheses of Structurally and Stereochemically Varied Forms of C                         7                         N Aminocyclitol Derivatives from Enzymatically Derived and Homochiral cis-1,2-Dihydrocatechols

Michael Dlugosch; Xinghua Ma; Shuxin Yang; Martin G. Banwell; Chenxi Ma; Jas S. Ward; Paul Carr

doi:10.1021/acs.orglett.8b03149

Syntheses of Structurally and Stereochemically Varied Forms of C ₇ N Aminocyclitol Derivatives from Enzymatically Derived and Homochiral cis-1,2-Dihydrocatechols

Michael Dlugosch, Xinghua Ma, Shuxin Yang, Martin G. Banwell^*, Chenxi Ma, Jas S. Ward, Paul Carr

^*Corresponding author for this work

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

14 Citations (Scopus)

Abstract

The structurally and stereoisomerically varied C ₇ N aminocyclitol derivatives 2-4 have been prepared, using a versatile and flexible range of protocols, from the cis-1,2-dihydrocatechols 5 and 6, homochiral metabolites derived from the whole-cell biotransformation of the corresponding halobenzene. Reaction sequences that enable syntheses of the enantiomeric forms of these derivatives have also been established.

Original language	English
Pages (from-to)	7225-7228
Number of pages	4
Journal	Organic Letters
Volume	20
Issue number	22
DOIs	https://doi.org/10.1021/acs.orglett.8b03149
Publication status	Published - 16 Nov 2018

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Dlugosch, M., Ma, X., Yang, S., Banwell, M. G., Ma, C., Ward, J. S., & Carr, P. (2018). Syntheses of Structurally and Stereochemically Varied Forms of C ₇ N Aminocyclitol Derivatives from Enzymatically Derived and Homochiral cis-1,2-Dihydrocatechols Organic Letters, 20(22), 7225-7228. https://doi.org/10.1021/acs.orglett.8b03149

Dlugosch, Michael ; Ma, Xinghua ; Yang, Shuxin et al. / Syntheses of Structurally and Stereochemically Varied Forms of C ₇ N Aminocyclitol Derivatives from Enzymatically Derived and Homochiral cis-1,2-Dihydrocatechols In: Organic Letters. 2018 ; Vol. 20, No. 22. pp. 7225-7228.

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title = " Syntheses of Structurally and Stereochemically Varied Forms of C 7 N Aminocyclitol Derivatives from Enzymatically Derived and Homochiral cis-1,2-Dihydrocatechols ",

abstract = " The structurally and stereoisomerically varied C 7 N aminocyclitol derivatives 2-4 have been prepared, using a versatile and flexible range of protocols, from the cis-1,2-dihydrocatechols 5 and 6, homochiral metabolites derived from the whole-cell biotransformation of the corresponding halobenzene. Reaction sequences that enable syntheses of the enantiomeric forms of these derivatives have also been established.",

author = "Michael Dlugosch and Xinghua Ma and Shuxin Yang and Banwell, \{Martin G.\} and Chenxi Ma and Ward, \{Jas S.\} and Paul Carr",

note = "Publisher Copyright: {\textcopyright} 2018 American Chemical Society.",

year = "2018",

month = nov,

day = "16",

doi = "10.1021/acs.orglett.8b03149",

language = "English",

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Dlugosch, M, Ma, X, Yang, S, Banwell, MG, Ma, C, Ward, JS & Carr, P 2018, ' Syntheses of Structurally and Stereochemically Varied Forms of C ₇ N Aminocyclitol Derivatives from Enzymatically Derived and Homochiral cis-1,2-Dihydrocatechols ', Organic Letters, vol. 20, no. 22, pp. 7225-7228. https://doi.org/10.1021/acs.orglett.8b03149

Syntheses of Structurally and Stereochemically Varied Forms of C ₇ N Aminocyclitol Derivatives from Enzymatically Derived and Homochiral cis-1,2-Dihydrocatechols . / Dlugosch, Michael; Ma, Xinghua; Yang, Shuxin et al.
In: Organic Letters, Vol. 20, No. 22, 16.11.2018, p. 7225-7228.

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

TY - JOUR

T1 - Syntheses of Structurally and Stereochemically Varied Forms of C 7 N Aminocyclitol Derivatives from Enzymatically Derived and Homochiral cis-1,2-Dihydrocatechols

AU - Dlugosch, Michael

AU - Ma, Xinghua

AU - Yang, Shuxin

AU - Banwell, Martin G.

AU - Ma, Chenxi

AU - Ward, Jas S.

AU - Carr, Paul

PY - 2018/11/16

Y1 - 2018/11/16

N2 - The structurally and stereoisomerically varied C 7 N aminocyclitol derivatives 2-4 have been prepared, using a versatile and flexible range of protocols, from the cis-1,2-dihydrocatechols 5 and 6, homochiral metabolites derived from the whole-cell biotransformation of the corresponding halobenzene. Reaction sequences that enable syntheses of the enantiomeric forms of these derivatives have also been established.

AB - The structurally and stereoisomerically varied C 7 N aminocyclitol derivatives 2-4 have been prepared, using a versatile and flexible range of protocols, from the cis-1,2-dihydrocatechols 5 and 6, homochiral metabolites derived from the whole-cell biotransformation of the corresponding halobenzene. Reaction sequences that enable syntheses of the enantiomeric forms of these derivatives have also been established.

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U2 - 10.1021/acs.orglett.8b03149

DO - 10.1021/acs.orglett.8b03149

M3 - Article

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VL - 20

SP - 7225

EP - 7228

JO - Organic Letters

JF - Organic Letters

IS - 22

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Dlugosch M, Ma X, Yang S, Banwell MG, Ma C, Ward JS et al. Syntheses of Structurally and Stereochemically Varied Forms of C ₇ N Aminocyclitol Derivatives from Enzymatically Derived and Homochiral cis-1,2-Dihydrocatechols Organic Letters. 2018 Nov 16;20(22):7225-7228. doi: 10.1021/acs.orglett.8b03149

Syntheses of Structurally and Stereochemically Varied Forms of C ₇ N Aminocyclitol Derivatives from Enzymatically Derived and Homochiral cis-1,2-Dihydrocatechols

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