Copper-Catalyzed C2- or C3-Thioglycosylation of Indoles with N‑(Thioglycosides)succinimides: An Effective Strategy for the Total Synthesis of Isatindigotindolosides

Isatindigotindolosides, indoles containing a 1-S-β-glucopyranosyl unit at position C2, show promising bioactivity. Here, we report a copper-catalyzed C2- or C3-thioglycosylation of indoles with N-(thioglycosides)­succinimides to construct indole alkaloid glucosides. This reaction is widely tolerant...

Full description

Saved in:
Bibliographic Details
Published inOrganic letters Vol. 25; no. 3; pp. 528 - 532
Main Authors Huang, Jie, Sun, Wen-Wu, Li, Jin-Quan, Ma, Ao-Di, Liu, Ji-Kai, Wu, Bin
Format Journal Article
LanguageEnglish
Published United States American Chemical Society 27.01.2023
Subjects
bioactive properties
glucosides
gramine
melatonin
Online AccessGet full text

Cover

Abstract Isatindigotindolosides, indoles containing a 1-S-β-glucopyranosyl unit at position C2, show promising bioactivity. Here, we report a copper-catalyzed C2- or C3-thioglycosylation of indoles with N-(thioglycosides)­succinimides to construct indole alkaloid glucosides. This reaction is widely tolerant of functional groups, as various indoles and thioglycosides are suitable. It also provides a reliable method for performing late-stage modifications of natural products, such as gramine and melatonin. Total syntheses of isatindigotindolosides I and II were successfully accomplished using the C2-thioglycosylation reaction as a key step.
AbstractList Isatindigotindolosides, indoles containing a 1-S-β-glucopyranosyl unit at position C2, show promising bioactivity. Here, we report a copper-catalyzed C2- or C3-thioglycosylation of indoles with N-(thioglycosides)­succinimides to construct indole alkaloid glucosides. This reaction is widely tolerant of functional groups, as various indoles and thioglycosides are suitable. It also provides a reliable method for performing late-stage modifications of natural products, such as gramine and melatonin. Total syntheses of isatindigotindolosides I and II were successfully accomplished using the C2-thioglycosylation reaction as a key step.
Isatindigotindolosides, indoles containing a 1-S-β-glucopyranosyl unit at position C2, show promising bioactivity. Here, we report a copper-catalyzed C2- or C3-thioglycosylation of indoles with N-(thioglycosides)succinimides to construct indole alkaloid glucosides. This reaction is widely tolerant of functional groups, as various indoles and thioglycosides are suitable. It also provides a reliable method for performing late-stage modifications of natural products, such as gramine and melatonin. Total syntheses of isatindigotindolosides I and II were successfully accomplished using the C2-thioglycosylation reaction as a key step.Isatindigotindolosides, indoles containing a 1-S-β-glucopyranosyl unit at position C2, show promising bioactivity. Here, we report a copper-catalyzed C2- or C3-thioglycosylation of indoles with N-(thioglycosides)succinimides to construct indole alkaloid glucosides. This reaction is widely tolerant of functional groups, as various indoles and thioglycosides are suitable. It also provides a reliable method for performing late-stage modifications of natural products, such as gramine and melatonin. Total syntheses of isatindigotindolosides I and II were successfully accomplished using the C2-thioglycosylation reaction as a key step.
Isatindigotindolosides, indoles containing a 1- -β-glucopyranosyl unit at position C2, show promising bioactivity. Here, we report a copper-catalyzed C2- or C3-thioglycosylation of indoles with -(thioglycosides)succinimides to construct indole alkaloid glucosides. This reaction is widely tolerant of functional groups, as various indoles and thioglycosides are suitable. It also provides a reliable method for performing late-stage modifications of natural products, such as gramine and melatonin. Total syntheses of isatindigotindolosides and were successfully accomplished using the C2-thioglycosylation reaction as a key step.
Author Huang, Jie
Li, Jin-Quan
Sun, Wen-Wu
Liu, Ji-Kai
Wu, Bin
Ma, Ao-Di
AuthorAffiliation Key Laboratory of Analytical Chemistry of the State Ethnic Affairs Commission
South-Central Minzu University
School of Pharmaceutical Sciences
AuthorAffiliation_xml – name: School of Pharmaceutical Sciences
– name: Key Laboratory of Analytical Chemistry of the State Ethnic Affairs Commission
– name: South-Central Minzu University
Author_xml – sequence: 1
  givenname: Jie
  surname: Huang
  fullname: Huang, Jie
  organization: School of Pharmaceutical Sciences
– sequence: 2
  givenname: Wen-Wu
  orcidid: 0000-0003-3687-9988
  surname: Sun
  fullname: Sun, Wen-Wu
  email: wenwusun@scuec.edu.cn
  organization: School of Pharmaceutical Sciences
– sequence: 3
  givenname: Jin-Quan
  surname: Li
  fullname: Li, Jin-Quan
  organization: School of Pharmaceutical Sciences
– sequence: 4
  givenname: Ao-Di
  surname: Ma
  fullname: Ma, Ao-Di
  organization: School of Pharmaceutical Sciences
– sequence: 5
  givenname: Ji-Kai
  orcidid: 0000-0001-6279-7893
  surname: Liu
  fullname: Liu, Ji-Kai
  email: liujikai@mail.scuec.edu.cn
  organization: School of Pharmaceutical Sciences
– sequence: 6
  givenname: Bin
  surname: Wu
  fullname: Wu, Bin
  email: 2015084@mail.scuec.edu.cn
  organization: South-Central Minzu University
BackLink https://www.ncbi.nlm.nih.gov/pubmed/36646633$$D View this record in MEDLINE/PubMed
BookMark eNqFUctuEzEUtVAr-oAvQEJetotJ_ZixZ9hVowKVqrJoWFuOx05cOXawPaDpil_gJ_gwvgSnSUFiUVbX9_o8pHNOwIEPXgPwBqMZRgRfSJVmIS6dznlGFKoJRy_AMW4IrThqyMGfN0NH4CSle4RwuXQvwRFlrGaM0mPwsw-bjY5VL7N004MeYE8qGCLsaTVf2bB0kwppcjLb4GEw8NoPwekEv9m8gre_vv84-wuzg07naVTKerveLu_gpYdXxmiV7VcN73KUWS8naIpBXmk4D8UV3k2-LMmmR_1UrPxgl2E7gtupvgKHRrqkX-_nKfj8_mref6xuPn247i9vKkl5mysmCUay5QwrpWmnDMcLLVuDVNso2shOogUbGGdccjUoQ-q2W6CupoPquDYtPQVnO91NDF9GnbJY26S0c9LrMCZBUV2CpoTh_0IJLyFT1KGmQN_uoeNirQexiXYt4ySeaiiAbgdQMaQUtRHK5sfIS2LWCYzEtnJRKhf7ysW-8sKl_3Cf5J9nXexY28_7MEZfYn2W8Rs4pMez
CitedBy_id crossref_primary_10_6023_cjoc202310026
crossref_primary_10_1021_acs_orglett_5c00219
crossref_primary_10_1021_acs_joc_3c02008
crossref_primary_10_1002_adsc_202300620
crossref_primary_10_1021_acs_joc_4c01136
crossref_primary_10_1021_acs_orglett_3c01798
Cites_doi 10.1021/acs.orglett.2c01657
10.1016/j.jep.2021.114648
10.1021/acs.orglett.0c01297
10.1080/10286020.2015.1117452
10.1039/C5CC05421D
10.1142/S0192415X1350050X
10.1080/10286020.2017.1320547
10.1021/acs.orglett.5b02743
10.1021/acs.joc.2c01326
10.1021/acs.joc.1c00448
10.1021/acs.orglett.8b02929
10.1021/acs.orglett.0c00207
10.1016/j.carres.2011.04.020
10.1039/D2OB00986B
10.1016/j.phytochem.2020.112337
10.1021/ol990763v
10.1002/1099-0690(200212)2002:23<3995::AID-EJOC3995>3.0.CO;2-P
10.1021/ol4036209
10.1021/jacs.8b11211
10.3389/fphar.2021.685575
10.1039/D1GC00591J
10.1021/acs.joc.0c01484
10.1080/10286020.2015.1055729
10.1002/anie.202012485
10.1021/acs.orglett.5b01889
10.1039/C7NJ02784B
10.1039/D1CC07143B
10.1021/acs.orglett.2c00353
10.1021/acs.orglett.8b01066
10.1039/C7SC04292B
10.1021/acs.orglett.7b03400
10.1039/D1CC03760A
10.1021/acs.orglett.0c03160
10.1021/acs.chemrev.8b00782
10.1002/anie.202004070
10.1098/rsos.180170
10.1021/jm051247f
10.1021/acs.joc.1c01378
10.1039/C5RA04965B
10.1016/j.jep.2020.112550
10.1021/acs.joc.0c00943
10.1002/ejoc.201200299
10.1021/acs.joc.6b02078
10.1111/brv.12140
10.1016/j.fitote.2021.104950
10.1021/acs.joc.1c02556
10.1016/j.fitote.2014.03.019
10.1002/adsc.202001202
10.1021/jo502402d
10.1039/C8GC01764F
ContentType Journal Article
Copyright 2023 American Chemical Society
Copyright_xml – notice: 2023 American Chemical Society
DBID AAYXX
CITATION
NPM
7X8
7S9
L.6
DOI 10.1021/acs.orglett.2c04270
DatabaseName CrossRef
PubMed
MEDLINE - Academic
AGRICOLA
AGRICOLA - Academic
DatabaseTitle CrossRef
PubMed
MEDLINE - Academic
AGRICOLA
AGRICOLA - Academic
DatabaseTitleList
MEDLINE - Academic
AGRICOLA
PubMed
Database_xml – sequence: 1
  dbid: NPM
  name: PubMed
  url: https://proxy.k.utb.cz/login?url=http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed
  sourceTypes: Index Database
DeliveryMethod fulltext_linktorsrc
Discipline Chemistry
EISSN 1523-7052
EndPage 532
ExternalDocumentID 36646633
10_1021_acs_orglett_2c04270
c15978906
Genre Journal Article
GroupedDBID ---
-DZ
-~X
.K2
123
4.4
55A
5VS
6P2
7~N
AABXI
ABFLS
ABFRP
ABMVS
ABPTK
ABQRX
ABUCX
ACGFS
ACS
ADHLV
AEESW
AENEX
AFEFF
AHGAQ
ALMA_UNASSIGNED_HOLDINGS
AQSVZ
BAANH
CS3
DU5
EBS
ED~
F5P
GGK
GNL
IH9
IHE
JG~
P2P
RNS
ROL
TN5
UI2
VF5
VG9
W1F
YNT
53G
AAHBH
AAYXX
ABBLG
ABJNI
ABLBI
CITATION
CUPRZ
NPM
7X8
7S9
L.6
ID FETCH-LOGICAL-a378t-6a210a8761cce39cf71bea8f0c85c35a9a0b6d6767a7cdcf2489b0943dc97ef83
IEDL.DBID ACS
ISSN 1523-7060
1523-7052
IngestDate Fri Jul 11 01:58:52 EDT 2025
Fri Jul 11 10:57:06 EDT 2025
Mon Jul 21 06:03:13 EDT 2025
Tue Jul 01 04:04:08 EDT 2025
Thu Apr 24 23:07:08 EDT 2025
Tue Jan 31 03:10:26 EST 2023
IsPeerReviewed true
IsScholarly true
Issue 3
Language English
License https://doi.org/10.15223/policy-029
https://doi.org/10.15223/policy-037
https://doi.org/10.15223/policy-045
LinkModel DirectLink
MergedId FETCHMERGED-LOGICAL-a378t-6a210a8761cce39cf71bea8f0c85c35a9a0b6d6767a7cdcf2489b0943dc97ef83
Notes ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ORCID 0000-0003-3687-9988
0000-0001-6279-7893
PMID 36646633
PQID 2766430905
PQPubID 23479
PageCount 5
ParticipantIDs proquest_miscellaneous_3040423261
proquest_miscellaneous_2766430905
pubmed_primary_36646633
crossref_citationtrail_10_1021_acs_orglett_2c04270
crossref_primary_10_1021_acs_orglett_2c04270
acs_journals_10_1021_acs_orglett_2c04270
ProviderPackageCode CITATION
AAYXX
PublicationCentury 2000
PublicationDate 2023-01-27
PublicationDateYYYYMMDD 2023-01-27
PublicationDate_xml – month: 01
  year: 2023
  text: 2023-01-27
  day: 27
PublicationDecade 2020
PublicationPlace United States
PublicationPlace_xml – name: United States
PublicationTitle Organic letters
PublicationTitleAlternate Org. Lett
PublicationYear 2023
Publisher American Chemical Society
Publisher_xml – name: American Chemical Society
References ref3/cit3
ref13/cit13a
ref16/cit16
ref13/cit13b
ref13/cit13c
ref13/cit13d
ref12/cit12d
ref12/cit12c
ref12/cit12b
ref12/cit12a
ref23/cit23
ref2/cit2c
ref2/cit2b
ref2/cit2a
ref1/cit1a
ref1/cit1b
ref17/cit17
ref10/cit10
ref19/cit19
ref11/cit11c
ref11/cit11b
ref11/cit11a
ref7/cit7b
ref7/cit7a
ref18/cit18
ref15/cit15a
ref15/cit15d
ref9/cit9b
ref15/cit15e
ref9/cit9a
ref15/cit15b
ref15/cit15c
ref8/cit8a
ref15/cit15f
ref8/cit8b
ref15/cit15g
ref21/cit21b
ref21/cit21a
ref5/cit5
ref4/cit4a
ref4/cit4b
ref4/cit4c
ref14/cit14a
ref14/cit14b
ref20/cit20a
ref22/cit22
ref20/cit20c
ref20/cit20b
ref6/cit6a
ref6/cit6b
References_xml – ident: ref13/cit13d
  doi: 10.1021/acs.orglett.2c01657
– ident: ref1/cit1b
  doi: 10.1016/j.jep.2021.114648
– ident: ref7/cit7b
  doi: 10.1021/acs.orglett.0c01297
– ident: ref4/cit4b
  doi: 10.1080/10286020.2015.1117452
– ident: ref15/cit15b
  doi: 10.1039/C5CC05421D
– ident: ref2/cit2b
  doi: 10.1142/S0192415X1350050X
– ident: ref4/cit4c
  doi: 10.1080/10286020.2017.1320547
– ident: ref11/cit11a
  doi: 10.1021/acs.orglett.5b02743
– ident: ref20/cit20c
  doi: 10.1021/acs.joc.2c01326
– ident: ref15/cit15c
  doi: 10.1021/acs.joc.1c00448
– ident: ref12/cit12d
  doi: 10.1021/acs.orglett.8b02929
– ident: ref14/cit14b
  doi: 10.1021/acs.orglett.0c00207
– ident: ref18/cit18
  doi: 10.1016/j.carres.2011.04.020
– ident: ref6/cit6a
  doi: 10.1039/D2OB00986B
– ident: ref5/cit5
  doi: 10.1016/j.phytochem.2020.112337
– ident: ref21/cit21b
  doi: 10.1021/ol990763v
– ident: ref22/cit22
  doi: 10.1002/1099-0690(200212)2002:23<3995::AID-EJOC3995>3.0.CO;2-P
– ident: ref15/cit15g
  doi: 10.1021/ol4036209
– ident: ref19/cit19
  doi: 10.1021/jacs.8b11211
– ident: ref1/cit1a
  doi: 10.3389/fphar.2021.685575
– ident: ref11/cit11b
  doi: 10.1039/D1GC00591J
– ident: ref20/cit20a
  doi: 10.1021/acs.joc.0c01484
– ident: ref4/cit4a
  doi: 10.1080/10286020.2015.1055729
– ident: ref13/cit13b
  doi: 10.1002/anie.202012485
– ident: ref15/cit15e
  doi: 10.1021/acs.orglett.5b01889
– ident: ref9/cit9a
  doi: 10.1039/C7NJ02784B
– ident: ref13/cit13c
  doi: 10.1039/D1CC07143B
– ident: ref12/cit12b
  doi: 10.1021/acs.orglett.2c00353
– ident: ref15/cit15f
  doi: 10.1021/acs.orglett.8b01066
– ident: ref7/cit7a
  doi: 10.1039/C7SC04292B
– ident: ref14/cit14a
  doi: 10.1021/acs.orglett.7b03400
– ident: ref15/cit15a
  doi: 10.1039/D1CC03760A
– ident: ref11/cit11c
  doi: 10.1021/acs.orglett.0c03160
– ident: ref6/cit6b
  doi: 10.1021/acs.chemrev.8b00782
– ident: ref12/cit12c
  doi: 10.1002/anie.202004070
– ident: ref9/cit9b
  doi: 10.1098/rsos.180170
– ident: ref23/cit23
  doi: 10.1021/jm051247f
– ident: ref12/cit12a
  doi: 10.1021/acs.joc.1c01378
– ident: ref8/cit8a
  doi: 10.1039/C5RA04965B
– ident: ref2/cit2c
  doi: 10.1016/j.jep.2020.112550
– ident: ref17/cit17
  doi: 10.1021/acs.joc.0c00943
– ident: ref16/cit16
  doi: 10.1002/ejoc.201200299
– ident: ref20/cit20b
  doi: 10.1021/acs.joc.6b02078
– ident: ref21/cit21a
  doi: 10.1111/brv.12140
– ident: ref2/cit2a
  doi: 10.1016/j.fitote.2021.104950
– ident: ref15/cit15d
  doi: 10.1021/acs.joc.1c02556
– ident: ref3/cit3
  doi: 10.1016/j.fitote.2014.03.019
– ident: ref13/cit13a
  doi: 10.1002/adsc.202001202
– ident: ref8/cit8b
  doi: 10.1021/jo502402d
– ident: ref10/cit10
  doi: 10.1039/C8GC01764F
SSID ssj0011529
Score 2.4416397
Snippet Isatindigotindolosides, indoles containing a 1-S-β-glucopyranosyl unit at position C2, show promising bioactivity. Here, we report a copper-catalyzed C2- or...
Isatindigotindolosides, indoles containing a 1- -β-glucopyranosyl unit at position C2, show promising bioactivity. Here, we report a copper-catalyzed C2- or...
SourceID proquest
pubmed
crossref
acs
SourceType Aggregation Database
Index Database
Enrichment Source
Publisher
StartPage 528
SubjectTerms bioactive properties
glucosides
gramine
melatonin
Title Copper-Catalyzed C2- or C3-Thioglycosylation of Indoles with N‑(Thioglycosides)succinimides: An Effective Strategy for the Total Synthesis of Isatindigotindolosides
URI http://dx.doi.org/10.1021/acs.orglett.2c04270
https://www.ncbi.nlm.nih.gov/pubmed/36646633
https://www.proquest.com/docview/2766430905
https://www.proquest.com/docview/3040423261
Volume 25
hasFullText 1
inHoldings 1
isFullTextHit
isPrint
link http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwjV1Lb9QwELZQOcCF92N5yUgcioSXxE4ch1sVURUk9tKt1FvkOA5ElHi1zh7SU_9C_wQ_jF_CTB7Ls1VPkSN7LHv8-OwZf0PIKxPKwpShAA1EcEBRMWepTSSLA66VqqKo7GMDflrIg6Po43F8_Ntj9b8s-Dx8q43HNLSinXODoSHghH6dS5jGiISyw63RALaitKdH5YIhKcxEMvR_IbgdGf_ndnQBxuz3mv3bZDG92BlcTL7ON20xN6f_EjherRl3yK0RddK9YZjcJddsc4_cyKZgb_fJ98ytVnbNMrzN6U5tSTPOqFvTTLDll9p9PumM893gOEddRT80PRUUxXtcuvhxdr77K1tdWv_ab4ypm_obJt7RvYYOPMmwuNKREbejAJgpAFC6dFArPewaSPja9_LRywg5ZB1-YIXupT4gR_vvl9kBG0M4MC0S1TKp4UipQVWhMVakpkrCwmpVBUbFRsQ61UEhSySN04kpTcUjlRbo7FiaNLGVEg_JTuMa-5jQOBa6Ai1XUpYRCFNRyAt8g5KqWEZSzMgu9HE-TkGf99Z1Hub4c-z4fOz4GeGT0nMzUqFjRI6Tywu92RZaDUwgl2d_OY2mHHSJZhjdWLfxOU8kwMAgDeKL8whYW9GELsMZeTQMxW2lAooDThRPrt7gp-QmB3CGV0c8eUZ22vXGPgcw1RYv-in0E6TNHqY
linkProvider American Chemical Society
linkToHtml http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwlV3NbtQwELZQOZQL5Z8tf0biUCSyJHbiONxWEdUW2r10V-otchwHIkqyWmcP6YlX4CV4MJ6EGSe7FYhWcIoc2eN_-7Nn_A0hr3Qgcl0EHHoghAOKjJiXmFh4kc-UlGUYFs434MlMTBfhh7PobHgUhm9hoBAWJFmnxL9kFwjeDv-gMu2YafQQAQf1mwBHGI7rSXq61R3AjpQ4llTGPeSG2XAN_V0I7kra_r4rXQE13ZZzuEcW28I6S5Mv43Wbj_XFHzyO_1ubO-T2gEHppB80d8kNU98ju-nG9dt98iNtlkuz8lK82-kuTEFT5tFmRVPuzT9XzafzTje2683oaFPSo9oRQ1G81aWzn9--H1xGqwpjX9u11lVdfcXAOzqpac-aDEstHfhxOwrwmQIcpfMGcqWnXQ0BW1knH22OkFG2wQ-s107qA7I4fD9Pp97g0MFTPJatJxQcMBWsv4HWhie6jIPcKFn6WkaaRypRfi4KpJBTsS50yUKZ5Gj6WOgkNqXkD8lO3dTmMaFRxFUJnV0KUYQgTIYBy_FFSiIjEQo-IgfQxtkwIW3mdO0syPDn0PDZ0PAjwjZ9n-mBGB39c5xfn-jNNtGy5wW5PvrLzaDKoC9RKaNq06xtxmIBoNBP_OjqOBxWWlSoi2BEHvUjcpsph-SAGvn-v1f4Bdmdzk-Os-Oj2ccn5BYD2IaXSix-Snba1do8A5jV5s_drPoFq-AnBw
linkToPdf http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwnV1Lb9QwELaqIgGX8oblaSQORSLbxE4ch9sqsGp5rJC6lcopchwHopZktc4e0hN_gT_BD-OXMONkF4FohThFjuzxY8b22DP-hpBnOhC5LgIOHAjhgCIj5iUmFl7kMyVlGYaFiw34fib2j8I3x9HxFpHrtzDQCAuUrDPi46xeFOWAMBDsDf-hQ-2YaYwSAYf1S2i4Q9mepIcb-wHsSolDSmXcQ3yYNd7Q34ngzqTt7zvTOeqm23am18jHTYOdt8nJeNXmY332B5bj__ToOtkZdFE66YXnBtky9U1yJV2HgLtFvqfNYmGWXop3PN2ZKWjKPNosacq9-eeq-XTa6cZ2vTsdbUp6UDuAKIq3u3T24-u33V_ZqsLY53aldVVXXzDxkk5q2qMnw5JLB5zcjoIaTUEtpfMGaqWHXQ0JW1lHH32PEFm2wQ-s247qbXI0fT1P970hsIOneCxbTyg4aCpYhwOtDU90GQe5UbL0tYw0j1Si_FwUCCWnYl3okoUyydEFstBJbErJ75DtuqnNPUKjiKsSGF4KUYRATIYBy_FlSiIjEQo-IrswxtkwMW3mbO4syPDnMPDZMPAjwtb8z_QAkI5xOk4vLvRiU2jR44NcnP3pWrAy4CUaZ1RtmpXNWCxAOfQTPzo_D4cVFw3rIhiRu71UbirlUBy0R37_3zv8hFz-8GqavTuYvX1ArjLQ3vBuicUPyXa7XJlHoG21-WM3sX4C84kpig
openUrl ctx_ver=Z39.88-2004&ctx_enc=info%3Aofi%2Fenc%3AUTF-8&rfr_id=info%3Asid%2Fsummon.serialssolutions.com&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.atitle=Copper-Catalyzed+C2-+or+C3-Thioglycosylation+of+Indoles+with+N+-%28Thioglycosides%29succinimides%3A+An+Effective+Strategy+for+the+Total+Synthesis+of+Isatindigotindolosides&rft.jtitle=Organic+letters&rft.au=Huang%2C+Jie&rft.au=Sun%2C+Wen-Wu&rft.au=Li%2C+Jin-Quan&rft.au=Ma%2C+Ao-Di&rft.date=2023-01-27&rft.issn=1523-7060&rft.eissn=1523-7052&rft.volume=25&rft.issue=3&rft.spage=528&rft.epage=532&rft_id=info:doi/10.1021%2Facs.orglett.2c04270&rft.externalDBID=n%2Fa&rft.externalDocID=10_1021_acs_orglett_2c04270
thumbnail_l http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/lc.gif&issn=1523-7060&client=summon
thumbnail_m http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/mc.gif&issn=1523-7060&client=summon
thumbnail_s http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/sc.gif&issn=1523-7060&client=summon