A convergent synthesis of Ro24-5913, a novel leukotriene D 4 antagonist

A new and convergent synthesis of the leukotriene D 4 antagonist Ro24-5913 (9) has been developed that can serve both for technical production and combinatorial strcture optimization. The synthesis of 6, achieved in 90% yield, is described. The conversion of 6 to 9 has been disclosed previously. A n...

Full description

Saved in:
Bibliographic Details
Published inTetrahedron letters Vol. 37; no. 31; pp. 5445 - 5448
Main Authors Maehr, Hubert, Yang, Roxana
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 29.07.1996
Elsevier
Subjects
Online AccessGet full text

Cover

Loading…
Abstract A new and convergent synthesis of the leukotriene D 4 antagonist Ro24-5913 (9) has been developed that can serve both for technical production and combinatorial strcture optimization. The synthesis of 6, achieved in 90% yield, is described. The conversion of 6 to 9 has been disclosed previously. A new, convergent synthesis of Ro24-5913, suited for technical production, is described.
AbstractList A new and convergent synthesis of the leukotriene D-4 antagonist Ro24-5913 (9) has been developed that can serve both for technical production and combinatorial structure optimization. The synthesis of 6, achieved in 90% yield, is described. The conversion of 6 to 9 has been disclosed previously. Copyright (C) 1996 Elsevier Science Ltd
A new and convergent synthesis of the leukotriene D 4 antagonist Ro24-5913 (9) has been developed that can serve both for technical production and combinatorial strcture optimization. The synthesis of 6, achieved in 90% yield, is described. The conversion of 6 to 9 has been disclosed previously. A new, convergent synthesis of Ro24-5913, suited for technical production, is described.
Author Yang, Roxana
Maehr, Hubert
Author_xml – sequence: 1
  givenname: Hubert
  surname: Maehr
  fullname: Maehr, Hubert
– sequence: 2
  givenname: Roxana
  surname: Yang
  fullname: Yang, Roxana
BookMark eNqNkE9Lw0AQxRepYFv9Bh72qGh09k-y2YtQqlahIIi9eFk2yaSu1l1JtpV-exNbPDuXx8B7w7zfiAx88EjIKYMrBiy7BpCQSBD6TGfnwJiGhB-QIcuVSESaswEZ_lmOyKht36GbLIchmU1oGfwGmyX6SNutj2_YupaGmj4HLpNUM3FJLfVhgyu6wvVHiI1Dj_SWSmp9tMvgXRuPyWFtVy2e7HVMFvd3L9OHZP40e5xO5gkyCTHBmhdM1oqnBa8gl5yrWklrWVWC5aqodVoXvLSZEDJVJc8VZ1BISLEoRFplYkzy3d1vLELdlt0rJZqvxn3aZmsmTOts8Zqp7Lfg1EUbXfDTsPaxi178P9q5b3Zu7NpsHDZmn6hcg2U0VXCGgen5mx6u6eEa3S09f8PFD_LXd1Q
ContentType Journal Article
Copyright 1996
Copyright_xml – notice: 1996
DBID 1KM
1KN
BLEPL
DTL
FCAKS
DOI 10.1016/0040-4039(96)01190-2
DatabaseName Index Chemicus
Current Chemical Reactions
Web of Science Core Collection
Science Citation Index Expanded
Web of Science - Science Citation Index Expanded - 1996
DatabaseTitle Web of Science
DatabaseTitleList Web of Science

Database_xml – sequence: 1
  dbid: 1KN
  name: Current Chemical Reactions
  url: https://proxy.k.utb.cz/login?url=https://www.webofscience.com/wos/woscc/search-with-editions?editions=WOS.CCR
  sourceTypes:
    Enrichment Source
    Index Database
DeliveryMethod fulltext_linktorsrc
Discipline Chemistry
EISSN 1873-3581
EndPage 5448
ExternalDocumentID A1996UZ67600006
0040403996011902
GroupedDBID ---
--K
--M
-ET
-~X
.GJ
.HR
.~1
0R~
123
186
1B1
1RT
1~.
1~5
29Q
3EH
4.4
457
4G.
53G
5VS
6TJ
7-5
71M
85S
8P~
9JM
9JN
AABNK
AACTN
AAEDT
AAEDW
AAIAV
AAIKJ
AAKOC
AALRI
AAOAW
AAQFI
AAQXK
AARLI
AATCM
AAXUO
AAYOK
ABFNM
ABFRF
ABGSF
ABJNI
ABMAC
ABPPZ
ABUDA
ABXDB
ABYKQ
ABZDS
ACBEA
ACBNA
ACDAQ
ACGFS
ACKIV
ACNCT
ACNNM
ACRLP
ADBBV
ADECG
ADEZE
ADMUD
ADUVX
AEBSH
AEFWE
AEHWI
AEKER
AENEX
AFFNX
AFKWA
AFMIJ
AFTJW
AFXIZ
AFZHZ
AGHFR
AGRDE
AGUBO
AGYEJ
AHHHB
AIEXJ
AIKHN
AITUG
AJBFU
AJOXV
AJSZI
ALCLG
ALMA_UNASSIGNED_HOLDINGS
AMFUW
AMRAJ
ASPBG
AVWKF
AXJTR
AZFZN
BKOJK
BLXMC
CS3
D0S
DOVZS
DU5
EBS
EFJIC
EFLBG
EJD
EO8
EO9
EP2
EP3
F5P
FDB
FEDTE
FGOYB
FIRID
FLBIZ
FNPLU
FYGXN
G-Q
G8K
GBLVA
HMS
HVGLF
HZ~
IH2
IHE
J1W
K-O
KOM
M2Z
M41
MO0
MVM
N9A
O-L
O9-
OAUVE
OGGZJ
OHT
OZT
P-8
P-9
P2P
PC.
Q38
R2-
RIG
RNS
ROL
RPZ
SCB
SCC
SDF
SDG
SDP
SES
SEW
SOC
SPC
SPCBC
SSK
SSP
SSU
SSZ
T5K
TN5
TWZ
UQL
WH7
WUQ
XFK
XJT
XPP
XSW
Y6R
YK3
YQJ
YR2
ZCG
ZKB
ZMT
ZXP
~02
~G-
~KM
1KM
1KN
AAHBH
AAXKI
ADVLN
AKRWK
BLEPL
DTL
GROUPED_WOS_SCIENCE_CITATION_INDEX_EXPANDED
ID FETCH-LOGICAL-e140t-ef2b14f725b2d084227f74aa1dc0a27bf95fb2ca633457c287210b405ebb35d63
IEDL.DBID AIKHN
ISICitedReferencesCount 10
ISICitedReferencesURI https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=CitingArticles&UT=A1996UZ67600006
ISSN 0040-4039
IngestDate Wed Sep 18 05:37:32 EDT 2024
Fri Oct 11 20:28:43 EDT 2024
Fri Feb 23 02:33:17 EST 2024
IsPeerReviewed true
IsScholarly true
Issue 31
Keywords WITTIG-HORNER REACTIONS
Language English
LinkModel DirectLink
LogoURL https://exlibris-pub.s3.amazonaws.com/fromwos-v2.jpg
MergedId FETCHMERGED-LOGICAL-e140t-ef2b14f725b2d084227f74aa1dc0a27bf95fb2ca633457c287210b405ebb35d63
PageCount 4
ParticipantIDs webofscience_primary_A1996UZ67600006
webofscience_primary_A1996UZ67600006CitationCount
elsevier_sciencedirect_doi_10_1016_0040_4039_96_01190_2
PublicationCentury 1900
PublicationDate 1996-07-29
PublicationDateYYYYMMDD 1996-07-29
PublicationDate_xml – month: 07
  year: 1996
  text: 1996-07-29
  day: 29
PublicationDecade 1990
PublicationPlace OXFORD
PublicationPlace_xml – name: OXFORD
PublicationTitle Tetrahedron letters
PublicationTitleAbbrev TETRAHEDRON LETT
PublicationYear 1996
Publisher Elsevier Ltd
Elsevier
Publisher_xml – name: Elsevier Ltd
– name: Elsevier
References Baimashev, B. A, Polezhaeva, N. A., Arbuzov, B. A, SU 1583425
Mouloungui, Elmestour, Delmas, Gaset (BIB11) 1992; 48
Baimashev, Polezhaeva, Arbuzov (BIB9) 1993; 63
Mouloungui, Murengezi, Gaset, Delmas (BIB15) 1988; 18
Villemin, Benalloum (BIB17) 1991; 21
Ramig, Dong, Van Arnum (BIB8) 1996; 37
Weferling, N., Kleiner, H.-J., EP-676406
Knott (BIB19) 1965
.
Seguineau, Villieras (BIB12) 1988; 29
Genet, Grisoni (BIB10) 1986; 27
Field, G., Vermeulen, J., Zally, W., US Patent 5,001,140, March 19, 1991.
Rao, Chakraborty, Reddy, Rao (BIB13) 1986; 35
O'Donnell, Crowley, Yaremko, O'Neill, Welton (BIB1) 1991; 259
122710.
Weferling, N., Kleiner, H.-J., EP-676407
Wharton, Wriggleswoth (BIB4) 1981
56316.
Moison, Texierboullet, Foucaud (BIB16) 1987; 43
Williams, Brooks, Moore, Stewart (BIB3) 1996; 37
56315.
Sinisterra, Barrios, Mouloungui, Delmas, Gaset (BIB14) 1991; 100
Bankova (BIB18) 1990; 53
BIB20
MOISON, H (WOS:A1987G224400010) 1987; 43
GENET, JP (WOS:A1986D731700020) 1986; 27
SINISTERRA, JV (WOS:A1991FB32800012) 1991; 100
RAO, AVR (WOS:A1994NX31700042) 1994; 35
BAIMASHEV BA (WOS:A1996UZ67600006.5) 1993; 63
BANKOVA, VS (WOS:A1990DX22500006) 1990; 53
WOS:A1996UZ67600006.3
ODONNELL, M (WOS:A1991GP82300042) 1991; 259
MOULOUNGUI, Z (WOS:A1988P616400009) 1988; 18
WOS:A1996UZ67600006.1
Ramig, K (WOS:A1996TQ74600008) 1996; 37
WHARTON, CJ (WOS:A1981LB95200019) 1981
VILLEMIN, D (WOS:A1991FG73200008) 1991; 21
WOS:A1996UZ67600006.2
WILLIAMS DR (WOS:A1996UZ67600006.19) 1996; 37
MOULOUNGUI, Z (WOS:A1992HD49900005) 1992; 48
KNOTT, EB (WOS:A19656580300049) 1965
SEGUINEAU, P (WOS:A1988M099200020) 1988; 29
(WOS:A1996UZ67600006.4) 1991
References_xml – volume: 259
  start-page: 751
  year: 1991
  end-page: 758
  ident: BIB1
  publication-title: J. Pharmacol. Exp. Ther.
  contributor:
    fullname: Welton
– volume: 100
  start-page: 267
  year: 1991
  end-page: 275
  ident: BIB14
  publication-title: Bull. Soc. Chim. Belg.
  contributor:
    fullname: Gaset
– volume: 27
  start-page: 4165
  year: 1986
  end-page: 4168
  ident: BIB10
  publication-title: Tetrahedron Lett.
  contributor:
    fullname: Grisoni
– volume: 18
  start-page: 1241
  year: 1988
  end-page: 1245
  ident: BIB15
  publication-title: Synthetic Commun.
  contributor:
    fullname: Delmas
– volume: 37
  start-page: 443
  year: 1996
  end-page: 446
  ident: BIB3
  publication-title: Tetrahedron Lett.
  contributor:
    fullname: Stewart
– ident: BIB20
– volume: 48
  start-page: 1219
  year: 1992
  end-page: 1232
  ident: BIB11
  publication-title: Tetrahedron
  contributor:
    fullname: Gaset
– start-page: 433
  year: 1981
  end-page: 436
  ident: BIB4
  publication-title: J. Chem. Soc., Perkin Trans. 1
  contributor:
    fullname: Wriggleswoth
– volume: 43
  start-page: 537
  year: 1987
  end-page: 542
  ident: BIB16
  publication-title: Tetrahedron
  contributor:
    fullname: Foucaud
– start-page: 3793
  year: 1965
  end-page: 3795
  ident: BIB19
  publication-title: J. Chem. Soc.
  contributor:
    fullname: Knott
– volume: 29
  start-page: 477
  year: 1988
  ident: BIB12
  publication-title: Tetrahedron Lett.
  contributor:
    fullname: Villieras
– volume: 37
  start-page: 443
  year: 1996
  end-page: 446
  ident: BIB8
  publication-title: Tetrahedron Lett.
  contributor:
    fullname: Van Arnum
– volume: 63
  start-page: 161
  year: 1993
  end-page: 162
  ident: BIB9
  publication-title: Russ. J. Gen. Chem.
  contributor:
    fullname: Arbuzov
– volume: 53
  start-page: 821
  year: 1990
  end-page: 824
  ident: BIB18
  publication-title: J. Nat. Products
  contributor:
    fullname: Bankova
– volume: 35
  start-page: 5043
  year: 1986
  end-page: 5046
  ident: BIB13
  publication-title: Tetrahedron Lett.
  contributor:
    fullname: Rao
– volume: 21
  start-page: 63
  year: 1991
  end-page: 68
  ident: BIB17
  publication-title: Synthetic Commun.
  contributor:
    fullname: Benalloum
– year: 1991
  ident: WOS:A1996UZ67600006.4
– ident: WOS:A1996UZ67600006.2
– ident: WOS:A1996UZ67600006.1
– ident: WOS:A1996UZ67600006.3
– volume: 37
  start-page: 443
  year: 1996
  ident: WOS:A1996UZ67600006.19
  publication-title: TETRAHEDRON LETT
  contributor:
    fullname: WILLIAMS DR
– volume: 37
  start-page: 443
  year: 1996
  ident: WOS:A1996TQ74600008
  article-title: A convenient preparation of cyclobutyl ketones: Naphthalene-catalyzed reductive cyclization of substituted 1,4-dihalobutanes
  publication-title: TETRAHEDRON LETTERS
  contributor:
    fullname: Ramig, K
– volume: 63
  start-page: 161
  year: 1993
  ident: WOS:A1996UZ67600006.5
  publication-title: RUSS J GEN CHEM
  contributor:
    fullname: BAIMASHEV BA
– volume: 21
  start-page: 63
  year: 1991
  ident: WOS:A1991FG73200008
  article-title: DRY REACTION UNDER MICROWAVE - CONDENSATION OF SULFONES WITH ALDEHYDES ON KF-ALUMINA
  publication-title: SYNTHETIC COMMUNICATIONS
  contributor:
    fullname: VILLEMIN, D
– volume: 100
  start-page: 267
  year: 1991
  ident: WOS:A1991FB32800012
  article-title: NEW CS2CO3 CATALYST FOR THE WITTIG-HORNER SYNTHESIS OF ACRYLATES IN INTERFACIAL SOLID LIQUID CONDITIONS
  publication-title: BULLETIN DES SOCIETES CHIMIQUES BELGES
  contributor:
    fullname: SINISTERRA, JV
– volume: 27
  start-page: 4165
  year: 1986
  ident: WOS:A1986D731700020
  article-title: ERGOLINE PRECURSORS .2. AN EFFICIENT SYNTHESIS OF C-RING BY PALLADIUM (0) CATALYZED-REACTIONS
  publication-title: TETRAHEDRON LETTERS
  contributor:
    fullname: GENET, JP
– volume: 35
  start-page: 5043
  year: 1994
  ident: WOS:A1994NX31700042
  article-title: AN EXPEDITIOUS APPROACH FOR THE SYNTHESIS OF BETA-HYDROXY ARYL ALPHA-AMINO-ACIDS PRESENT IN VANCOMYCIN
  publication-title: TETRAHEDRON LETTERS
  contributor:
    fullname: RAO, AVR
– volume: 48
  start-page: 1219
  year: 1992
  ident: WOS:A1992HD49900005
  article-title: WITTIG-HORNER REACTIONS AND TRANSESTERIFICATION BY ANIONIC ACTIVATION OF C-H AND O-H BONDS IN A HETEROGENEOUS POTASSIUM CARBONATE-ALCOHOL SOLUTION
  publication-title: TETRAHEDRON
  contributor:
    fullname: MOULOUNGUI, Z
– volume: 29
  start-page: 477
  year: 1988
  ident: WOS:A1988M099200020
  article-title: THE WITTIG-HORNER REACTION IN HETEROGENEOUS MEDIA .10. SYNTHESIS OF ALPHA-DEUTERATED FUNCTIONAL OLEFINS USING POTASSIUM CARBONATE WITH DEUTERIUM-OXIDE
  publication-title: TETRAHEDRON LETTERS
  contributor:
    fullname: SEGUINEAU, P
– volume: 53
  start-page: 821
  year: 1990
  ident: WOS:A1990DX22500006
  article-title: SYNTHESIS OF NATURAL ESTERS OF SUBSTITUTED CINNAMIC-ACIDS
  publication-title: JOURNAL OF NATURAL PRODUCTS
  contributor:
    fullname: BANKOVA, VS
– volume: 259
  start-page: 751
  year: 1991
  ident: WOS:A1991GP82300042
  article-title: PHARMACOLOGICAL ACTIONS OF RO 24-5913, A NOVEL ANTAGONIST OF LEUKOTRIENE-D(4)
  publication-title: JOURNAL OF PHARMACOLOGY AND EXPERIMENTAL THERAPEUTICS
  contributor:
    fullname: ODONNELL, M
– start-page: 433
  year: 1981
  ident: WOS:A1981LB95200019
  article-title: INHIBITORS OF PYRIMIDINE BIOSYNTHESIS .2. THE SYNTHESIS OF AMIDINE PHOSPHONATES AS POTENTIAL INHIBITORS OF CARBAMOYL PHOSPHATE SYNTHASE
  publication-title: JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1
  contributor:
    fullname: WHARTON, CJ
– volume: 18
  start-page: 1241
  year: 1988
  ident: WOS:A1988P616400009
  article-title: CESIUM CARBONATE IN WEAKLY HYDRATED SOLID-LIQUID HETEROGENEOUS MEDIUM - A NEW REAGENT FOR ANIONIC ACTIVATION SYNTHESIS
  publication-title: SYNTHETIC COMMUNICATIONS
  contributor:
    fullname: MOULOUNGUI, Z
– volume: 43
  start-page: 537
  year: 1987
  ident: WOS:A1987G224400010
  article-title: KNOEVENAGEL, WITTIG AND WITTIG-HORNER REACTIONS IN THE PRESENCE OF MAGNESIUM-OXIDE OR ZINC-OXIDE
  publication-title: TETRAHEDRON
  contributor:
    fullname: MOISON, H
– start-page: 3793
  year: 1965
  ident: WOS:A19656580300049
  article-title: SYNTHESIS OF HETEROCYCLIC ALKENES BY HORNER REACTION
  publication-title: JOURNAL OF THE CHEMICAL SOCIETY
  contributor:
    fullname: KNOTT, EB
SSID ssj0000680
Score 1.5848323
Snippet A new and convergent synthesis of the leukotriene D 4 antagonist Ro24-5913 (9) has been developed that can serve both for technical production and...
A new and convergent synthesis of the leukotriene D-4 antagonist Ro24-5913 (9) has been developed that can serve both for technical production and...
Source Web of Science
SourceID webofscience
elsevier
SourceType Enrichment Source
Index Database
Publisher
StartPage 5445
SubjectTerms Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
Title A convergent synthesis of Ro24-5913, a novel leukotriene D 4 antagonist
URI https://dx.doi.org/10.1016/0040-4039(96)01190-2
http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=FullRecord&UT=A1996UZ67600006
Volume 37
WOS A1996UZ67600006
WOSCitedRecordID wosA1996UZ67600006
hasFullText 1
inHoldings 1
isFullTextHit
isPrint
link http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwnV1LS8NAEF60PehFfGJ9lD30oODa7COb7LHUR1XsQSwULyGbbKRYkmJTwYu_3dk8pAUPIjllScLyzWa-GXbmW4Q6mpuEwkogxncdIlwNvxSPDQRywMU8UUwWavuPQzkYifuxO17qhbFllZXvL3164a2rkW6FZnc2mVhVHri4VRehwGrghpvARkI0ULN39zAYLvlj36lr5-wLdQMdld2fsTMlz4vPELbCSr-QUUE8N9toq4oYca-c1A5aM-ku2ujXB7XtodseLmrHbRtljuefKcR088kcZwl-ypggrqL8Aoc4zT7MFE_N4i2zp2ilBl9hgQHZ8DWz-rn7aHRz_dwfkOp8BGIgLcqJSZimIvGYq1ns-IIxL_FEGNI4ckLm6US5iWZRKDkXrhdBbgT5nYYIzWjN3VjyA9RIs9QcIuwbT_nUKKGpEpKD4XRsFI0VZCwR0FwLeTUowYp5AvC8QV0pZuEMLJyBghsLZ8BaqLOMYTArRTQCK7crRy_SbgyCiVqI_uWxfiVcbhv286N_T-oYbZbV1x5h6gQ18veFOYXgItdttH75RdvVGvoG6_zHEQ
link.rule.ids 315,786,790,4521,24144,27955,27956,45618,45712
linkProvider Elsevier
linkToHtml http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwnV3LS8MwGA8yD_MiPnE-c9hBwbrl0bQ5jumcuu0gGwwvoVlTGY52uE7w4t_ulz5kAw8iPTWEEn5f8j3o7_sFobpmJiKwExzju02HuxqOFAsNJHIQi1kkqcjU9vsD0R3xx7E7XumFsbTKwvfnPj3z1sVIo0CzMZ9OrSoPPMyqixCIauCGN20yYGldN19kxRv7zZI5Z6eX7XNENH7GLqW4yj7i0LWY9EsoysJOZwdtF_kibuVL2kUbJt5D1XZ5Tds-um_hjDlumyhTvPiMIaNbTBc4ifBzQrnjSsKucYDj5MPM8Mws3xJ7h1Zs8C3mGHANXhOrnnuARp27YbvrFLcjOAaKotQxEdWERx51NQ2bPqfUizweBCScNAPq6Ui6kaaTQDDGXW8ClRFUdxryM6M1c0PBDlElTmJzhLBvPOkTI7kmkgsGZtOhkSSUUK9MIMjVkFeCotaMo8DvqpInZuFUFk4l4cXCqWgN1VcxVPNcQkNZsV0xehH2tyCYqIbIX6a1C9ly266fHv97UReo2h32e6r3MHg6QVs5D9tzqDxFlfR9ac4gzUj1ebaPvgGf5sfm
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=A+convergent+synthesis+of+Ro24-5913%2C+a+novel+leukotriene+D+4+antagonist&rft.jtitle=Tetrahedron+letters&rft.au=Maehr%2C+Hubert&rft.au=Yang%2C+Roxana&rft.date=1996-07-29&rft.pub=Elsevier+Ltd&rft.issn=0040-4039&rft.eissn=1873-3581&rft.volume=37&rft.issue=31&rft.spage=5445&rft.epage=5448&rft_id=info:doi/10.1016%2F0040-4039%2896%2901190-2&rft.externalDocID=0040403996011902
thumbnail_l http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/lc.gif&issn=0040-4039&client=summon
thumbnail_m http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/mc.gif&issn=0040-4039&client=summon
thumbnail_s http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/sc.gif&issn=0040-4039&client=summon