Enantioselective total synthesis of eudesma-3,11(13)-dien-12-oic acid

The first enantioselective total synthesis of eudesma-3,11(13)-dien-12-oic acid 1 was achieved starting from (+)-dihydrocarvone in ten steps.

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Published inSynthesis (Stuttgart) no. 9; pp. 1305 - 1307
Main Authors Chen, YG, Zhou, G, Liu, LJ, Xiong, ZM, Li, YL
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 2001
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
enantioselective synthesis
12-eudesma-3,11-dien-12-oic acid
sesquiterpenes
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Abstract The first enantioselective total synthesis of eudesma-3,11(13)-dien-12-oic acid 1 was achieved starting from (+)-dihydrocarvone in ten steps.
AbstractList The first enantioselective total synthesis of eudesma-3,11(13)-dien-12-oic acid 1 was achieved starting from (+)-dihydrocarvone in ten steps.
Author Li, YL
Liu, LJ
Chen, YG
Xiong, ZM
Zhou, G
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Issue 9
Keywords enantioselective synthesis
12-eudesma-3,11-dien-12-oic acid
sesquiterpenes
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References CHETTY, GL (WOS:A19668010300036) 1966; 22
Xiong, ZM (WOS:A1996VG66900029) 1996; 7
SHTACHER, G (WOS:A1970H633100047) 1970; 13
BOSE, AK (WOS:A1973Q690300014) 1973
BARBETTI, P (WOS:A1985ATT6000046) 1985; 51
CECCHERELLI, P (WOS:A1985AWF5400041) 1985; 24
COREY, EJ (WOS:A19657118700037) 1965; 87
Chen, YG (WOS:000074547600017) 1998; 9
References_xml – volume: 51
  start-page: 471
  year: 1985
  ident: WOS:A1985ATT6000046
  article-title: A NEW EUDESMANE ACID FROM DITTRICHIA-(INULA)-VISCOSA
  publication-title: PLANTA MEDICA
  contributor:
    fullname: BARBETTI, P
– start-page: 3937
  year: 1973
  ident: WOS:A1973Q690300014
  article-title: FACILE REPLACEMENT OF HYDROXYL BY HALOGEN WITH INVERSION - STEROIDS .10.
  publication-title: TETRAHEDRON LETTERS
  contributor:
    fullname: BOSE, AK
– volume: 13
  start-page: 1221
  year: 1970
  ident: WOS:A1970H633100047
  article-title: 12-CARBOXYEUDESMA-3,11(13)-DIENE - A NOVEL SESQUITERPENIC ACID WITH A NARROW ANTIFUNGAL SPECTRUM
  publication-title: JOURNAL OF MEDICINAL CHEMISTRY
  contributor:
    fullname: SHTACHER, G
– volume: 87
  start-page: 5736
  year: 1965
  ident: WOS:A19657118700037
  article-title: TOTAL SYNTHESIS OF DIHYDROCOSTUNOLIDE
  publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
  contributor:
    fullname: COREY, EJ
– volume: 9
  start-page: 1923
  year: 1998
  ident: WOS:000074547600017
  article-title: Total synthesis and stereochemistry of 13-hydroxy-alpha-eudesmol
  publication-title: TETRAHEDRON-ASYMMETRY
  contributor:
    fullname: Chen, YG
– volume: 22
  start-page: 2311
  year: 1966
  ident: WOS:A19668010300036
  article-title: STUDIES IN SESQUITERPENES .25. A SYNTHESIS OF ALPHA-SELINENE
  publication-title: TETRAHEDRON
  contributor:
    fullname: CHETTY, GL
– volume: 24
  start-page: 2987
  year: 1985
  ident: WOS:A1985AWF5400041
  article-title: SESQUITERPENE ACIDS FROM DITTRICHIA-VISCOSA
  publication-title: PHYTOCHEMISTRY
  contributor:
    fullname: CECCHERELLI, P
– volume: 7
  start-page: 2607
  year: 1996
  ident: WOS:A1996VG66900029
  article-title: An efficient asymmetric route to eudesmane acids. Total synthesis of (+)-12-hydroxy-alpha-cyperone, (+)-12-oxo-alpha-cyperone and (+)-3-oxoeudesma-4,11(13)-dien-12-oic acid
  publication-title: TETRAHEDRON-ASYMMETRY
  contributor:
    fullname: Xiong, ZM
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Snippet The first enantioselective total synthesis of eudesma-3,11(13)-dien-12-oic acid 1 was achieved starting from (+)-dihydrocarvone in ten steps.
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Chemistry, Organic
Physical Sciences
Science & Technology
Title Enantioselective total synthesis of eudesma-3,11(13)-dien-12-oic acid
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