Bicyclomangostin: a new acid-catalysed cyclization product from mangostin

Cyclization of mangostin with p-toluenesulfonic acid gave 1-isomangostin, 3-isomangostin, and a new cyclization product, bicyclomangostin (4). The structure of bicyclomangostin was determined by spectroscopic and X-ray crystallographic studies. The methyl ether derivatives (8) and (9) or (10) were p...

Full description

Saved in:
Bibliographic Details
Published inAustralian journal of chemistry Vol. 51; no. 3; pp. 249 - 254
Main Authors Mahabusarakam, W, Pakawatchai, C, Wiriyachitra, P, Taylor, WC, Skelton, BW, White, AH
Format Journal Article
LanguageEnglish
Published COLLINGWOOD C S I R O PUBLICATIONS 01.01.1998
Subjects
Online AccessGet more information

Cover

Loading…
Abstract Cyclization of mangostin with p-toluenesulfonic acid gave 1-isomangostin, 3-isomangostin, and a new cyclization product, bicyclomangostin (4). The structure of bicyclomangostin was determined by spectroscopic and X-ray crystallographic studies. The methyl ether derivatives (8) and (9) or (10) were produced on methylation of bicyclomangostin, depending on the method used.
AbstractList Cyclization of mangostin with p-toluenesulfonic acid gave 1-isomangostin, 3-isomangostin, and a new cyclization product, bicyclomangostin (4). The structure of bicyclomangostin was determined by spectroscopic and X-ray crystallographic studies. The methyl ether derivatives (8) and (9) or (10) were produced on methylation of bicyclomangostin, depending on the method used.
Author Taylor, WC
Pakawatchai, C
Wiriyachitra, P
Skelton, BW
White, AH
Mahabusarakam, W
Author_xml – sequence: 1
  givenname: W
  surname: Mahabusarakam
  fullname: Mahabusarakam, W
– sequence: 2
  givenname: C
  surname: Pakawatchai
  fullname: Pakawatchai, C
– sequence: 3
  givenname: P
  surname: Wiriyachitra
  fullname: Wiriyachitra, P
– sequence: 4
  givenname: WC
  surname: Taylor
  fullname: Taylor, WC
– sequence: 5
  givenname: BW
  orcidid: 0000-0002-1515-6636
  surname: Skelton
  fullname: Skelton, BW
– sequence: 6
  givenname: AH
  surname: White
  fullname: White, AH
BookMark eNqNj0tLAzEcxHOoYFv1M-Quq0ma13rTxUeh4EXPJfknkcg2KZuUsn561weePc0M_GZgFmiWcvIIXVByRYmi112riGxnaE4I4U3LmThFi1LeCaFcMj1H67sII_R5Z9JbLjWmG2xw8kdsILoGTDX9WLzDX1D8MDXmhPdDdgeoOAx5h_-KZ-gkmL74819doteH-5fuqdk8P667200DjIvaaMtBGCmVVC5wo_wUhBVCh-CVZa0URHiqgwTg3rZsxZy1NlhhLAMHhC3R5c_u0dscCkSfwG_3Q9yZYdxOP4laMaHZZCidaP1_uov1-2GXD6myT3lNYu4
CitedBy_id crossref_primary_10_1016_S0040_4039_01_02137_2
crossref_primary_10_1080_10715760000301161
crossref_primary_10_1016_S0040_4039_02_01630_1
crossref_primary_10_1002_chin_199835224
crossref_primary_10_1016_j_molcatb_2014_02_010
crossref_primary_10_1016_S0040_4020_03_01136_0
ContentType Journal Article
DBID 1KM
BLEPL
DTL
FFIDB
DOI 10.1071/C97069
DatabaseName Index Chemicus
Web of Science Core Collection
Science Citation Index Expanded
Web of Science - Science Citation Index Expanded - 1998
DatabaseTitle Web of Science
DatabaseTitleList Web of Science
Database_xml – sequence: 1
  dbid: 1KM
  name: Index Chemicus
  url: https://proxy.k.utb.cz/login?url=https://www.webofscience.com/wos/woscc/search-with-editions?editions=WOS.IC
  sourceTypes:
    Enrichment Source
    Index Database
DeliveryMethod no_fulltext_linktorsrc
Discipline Chemistry
EndPage 254
ExternalDocumentID 000073258200011
GroupedDBID -~X
0R~
1KM
23N
4.4
53G
5GY
8WZ
A6W
ABEFU
ABPPZ
ACNCT
AEIBA
AENEX
AI.
ALMA_UNASSIGNED_HOLDINGS
BLEPL
CAG
COF
CS3
DTL
EBS
EJD
F5P
GROUPED_WOS_SCIENCE_CITATION_INDEX_EXPANDED
H~9
L7B
MV1
RCO
TN5
TWZ
UPT
VH1
WH7
ZCG
~02
~KM
ID FETCH-LOGICAL-c245t-8b4c5a66767df4a7e5a65b558ffe7b296505e18f6cc4eb9232dbbbfb5ab2cdc02
ISICitedReferencesCount 7
ISICitedReferencesURI https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=CitingArticles&UT=000073258200011
ISSN 0004-9425
IngestDate Tue Sep 17 23:36:14 EDT 2024
Wed Sep 18 03:49:13 EDT 2024
IsPeerReviewed true
IsScholarly true
Issue 3
Language English
LinkModel OpenURL
LogoURL https://exlibris-pub.s3.amazonaws.com/fromwos-v2.jpg
MergedId FETCHMERGED-LOGICAL-c245t-8b4c5a66767df4a7e5a65b558ffe7b296505e18f6cc4eb9232dbbbfb5ab2cdc02
ORCID 0000-0002-1515-6636
PageCount 6
ParticipantIDs webofscience_primary_000073258200011
webofscience_primary_000073258200011CitationCount
PublicationCentury 1900
PublicationDate 1998-01-01
PublicationDateYYYYMMDD 1998-01-01
PublicationDate_xml – month: 01
  year: 1998
  text: 1998-01-01
  day: 01
PublicationDecade 1990
PublicationPlace COLLINGWOOD
PublicationPlace_xml – name: COLLINGWOOD
PublicationTitle Australian journal of chemistry
PublicationTitleAbbrev AUST J CHEM
PublicationYear 1998
Publisher C S I R O PUBLICATIONS
Publisher_xml – name: C S I R O PUBLICATIONS
References YATES, P (WOS:A1970F698400024) 1970; 48
YATES, P (WOS:A19679606400007) 1967; 23
HALL SR (WOS:000073258200011.8) 1987
DUTTA, PK (WOS:A1987H306400029) 1987; 26
STOUT GH (WOS:000073258200011.4) 1968
YATES, P (WOS:A1958WB38200046) 1958; 80
SCHMID W (WOS:000073258200011.1) 1855; 93
WIRIYACHITRA P (WOS:000073258200011.3) 1986; 12
References_xml – volume: 93
  start-page: 83
  year: 1855
  ident: WOS:000073258200011.1
  publication-title: LIEBIGS ANN CHEM
  contributor:
    fullname: SCHMID W
– year: 1987
  ident: WOS:000073258200011.8
  publication-title: XTAL 2 2 USERS MANUA
  contributor:
    fullname: HALL SR
– start-page: 211
  year: 1968
  ident: WOS:000073258200011.4
  publication-title: J CHEM SOC CHEM COMM
  contributor:
    fullname: STOUT GH
– volume: 26
  start-page: 281
  year: 1987
  ident: WOS:A1987H306400029
  article-title: ACID-CATALYZED CYCLIZATIONS OF XANTHONES - STRUCTURE OF A NEW XANTHONE FROM GARCINIA-MANGOSTANA LINN
  publication-title: INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY
  contributor:
    fullname: DUTTA, PK
– volume: 23
  start-page: 3307
  year: 1967
  ident: WOS:A19679606400007
  article-title: DIMETHYLMANGOSTIN HYDROCHLORIDE
  publication-title: TETRAHEDRON
  contributor:
    fullname: YATES, P
– volume: 12
  start-page: 233
  year: 1986
  ident: WOS:000073258200011.3
  publication-title: J SCI SOC THAILAND
  contributor:
    fullname: WIRIYACHITRA P
– volume: 48
  start-page: 680
  year: 1970
  ident: WOS:A1970F698400024
  article-title: ACID-CATALYZED CYCLIZATION OF MANGOSTIN
  publication-title: CANADIAN JOURNAL OF CHEMISTRY
  contributor:
    fullname: YATES, P
– volume: 80
  start-page: 1691
  year: 1958
  ident: WOS:A1958WB38200046
  article-title: THE STRUCTURE OF MANGOSTIN
  publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
  contributor:
    fullname: YATES, P
SSID ssj0014628
Score 1.5509526
Snippet Cyclization of mangostin with p-toluenesulfonic acid gave 1-isomangostin, 3-isomangostin, and a new cyclization product, bicyclomangostin (4). The structure of...
Source Web of Science
SourceID webofscience
SourceType Enrichment Source
Index Database
StartPage 249
SubjectTerms Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
Title Bicyclomangostin: a new acid-catalysed cyclization product from mangostin
URI http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=FullRecord&UT=000073258200011
Volume 51
WOS 000073258200011
WOSCitedRecordID wos000073258200011
hasFullText
inHoldings 1
isFullTextHit
isPrint
link http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwnV1NT9wwELWW9gAX1BYQ0A_5wC1K2XjtJO6tRK2gFUWiILghexxD1LKL2FTV8usZx_nahcO2l2g3SrIrz2T8Zuz3hpA9nNOMxqkk1GBlyCGOQmnsCF-8oTFDSJkEx3c-_hEfnvNvl-JyMHjos0tK_REenuWV_I9V8Rza1bFk_8Gy7UPxBH5G--IRLYzHpWx8UMAMfk9u1fh6MnVqABVzGYFyoKAwYVWamU0RUrrLasKl25HlNF49saS9tQ9Se_WPnrAENK3huiL2jdJ_pupe_fJe1ZZrEJaqvxjj617XbSH2orgvZm73Zll1N-q4ZV3d4CLr6hCemDdXh8iCn8FRcBqczLGg50IvDyX3LOcm9NZas0U_M_dx1OuY1lMy8zrTT6I9wiOnIiyTYSy7-axZw1-Y5trNh9Xq7YiJlFWAeIWsJKmLjdH343b9yTF2feLk_3TTlSqJ9v3PPYtTKkxy9oqs18kE_ew94zUZ5OM3ZDVrDLVBjhY95BNVFP2DzvsH7fkHrf2DOv-g7Y2b5Pzrl7PsMKybZ4TAuCjDVHMQyu1gTozlKsnxi9BCpNbmiWYSkbnIo9TGADzXCPOZ0VpbLZRmYGDItsiL8WScbxOaxIB5Mea6VituJJfAFMOxsDg6IEZyh-z1x-LqzuukXC0M9A6Jlrksq7XpnSZDubvco9-Stc4l35GXFl_w_D2ixVJ_qAz7CAY8bJo
link.rule.ids 786
linkProvider Clarivate
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=Bicyclomangostin%3A+a+new+acid-catalysed+cyclization+product+from+mangostin&rft.jtitle=Australian+journal+of+chemistry&rft.au=Mahabusarakam%2C+W&rft.au=Pakawatchai%2C+C&rft.au=Wiriyachitra%2C+P&rft.au=Taylor%2C+WC&rft.date=1998-01-01&rft.pub=C+S+I+R+O+PUBLICATIONS&rft.issn=0004-9425&rft.volume=51&rft.issue=3&rft.spage=249&rft.epage=254&rft_id=info:doi/10.1071%2FC97069&rft.externalDBID=n%2Fa&rft.externalDocID=000073258200011
thumbnail_l http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/lc.gif&issn=0004-9425&client=summon
thumbnail_m http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/mc.gif&issn=0004-9425&client=summon
thumbnail_s http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/sc.gif&issn=0004-9425&client=summon