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WO2006133395A3 - Stereoselective reduction of triterpenones - Google Patents

Stereoselective reduction of triterpenones Download PDF

Info

Publication number
WO2006133395A3
WO2006133395A3 PCT/US2006/022422 US2006022422W WO2006133395A3 WO 2006133395 A3 WO2006133395 A3 WO 2006133395A3 US 2006022422 W US2006022422 W US 2006022422W WO 2006133395 A3 WO2006133395 A3 WO 2006133395A3
Authority
WO
WIPO (PCT)
Prior art keywords
methods
triterpenones
stereoselective reduction
triterpen
oleanan
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/US2006/022422
Other languages
French (fr)
Other versions
WO2006133395A2 (en
Inventor
Pavel A Krasutsky
Kalyan Munshi
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
University of Minnesota Twin Cities
University of Minnesota System
Original Assignee
University of Minnesota Twin Cities
University of Minnesota System
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by University of Minnesota Twin Cities, University of Minnesota System filed Critical University of Minnesota Twin Cities
Publication of WO2006133395A2 publication Critical patent/WO2006133395A2/en
Publication of WO2006133395A3 publication Critical patent/WO2006133395A3/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J63/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by expansion of only one ring by one or two atoms
    • C07J63/008—Expansion of ring D by one atom, e.g. D homo steroids

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Steroid Compounds (AREA)

Abstract

The present invention provides for methods of selectively converting triterpen-3-ones to the corresponding triterpen-3-ols. The selectivity of the methods is at least about 80% of the beta-isomer, at the C-3 position. Specifically, the present invention provides for methods of preparing betulinic acid, lupeol, betulin, allobetulin, and oleanan-3-β-ol-28,19-lactone from betulonic acid, lupeone, betulone, allobetulone and oleanan-3-β-one-28,19- lactone, respectively.
PCT/US2006/022422 2005-06-08 2006-06-07 Stereoselective reduction of triterpenones Ceased WO2006133395A2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US68873905P 2005-06-08 2005-06-08
US60/688,739 2005-06-08

Publications (2)

Publication Number Publication Date
WO2006133395A2 WO2006133395A2 (en) 2006-12-14
WO2006133395A3 true WO2006133395A3 (en) 2007-03-01

Family

ID=37398814

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2006/022422 Ceased WO2006133395A2 (en) 2005-06-08 2006-06-07 Stereoselective reduction of triterpenones

Country Status (1)

Country Link
WO (1) WO2006133395A2 (en)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2231163A4 (en) * 2007-12-04 2012-10-31 Myriad Pharmaceuticals Inc Compounds and therapeutic use thereof
KR101213174B1 (en) 2010-03-19 2012-12-18 주식회사 동일팜텍 Composition for anti-obesity or reducing body-fat
CN102703529B (en) * 2012-06-15 2014-01-22 郑州轻工业学院 Method for generating betulinic ketone alcohol by catalyzing betulin through rhodotorula mucilaginosa
CN104761460B (en) * 2015-03-26 2017-06-20 苏州沪云肿瘤研究中心股份有限公司 Glaucocalyxin A derivative and preparation method and application thereof
CN106560473B (en) * 2016-11-09 2018-01-12 泰州学院 A kind of improved Bardoxolone lactone derivatives synthesis technique
EP4249057A3 (en) 2018-01-04 2023-11-29 Amryt Research Limited Betulin-containing birch bark extracts and their formulation

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1308435A2 (en) * 2001-10-31 2003-05-07 Kanto Kagaku Kabushiki Kaisha Process for producing optically active amino alcohols

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1308435A2 (en) * 2001-10-31 2003-05-07 Kanto Kagaku Kabushiki Kaisha Process for producing optically active amino alcohols

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
ALLSOP ET AL: "Infrared Spectra of Natural Products. Part VI. The Characterisation of Equatorial and Axial 3-Hydroxy Groups in Triterpenoids", JOURNAL OF THE CHEMICAL SOCIETY., 1956, GBCHEMICAL SOCIETY. LETCHWORTH., pages 4868 - 4873, XP002408123 *
O. JEGER ET AL: "Zur Kenntnis der Triterpene. (118. Mitteilung) Herstellung der epimeren Lupanole-4 und des epi-Lupanols-2", HELVETICA CHIMICA ACTA., vol. 30, no. 6, 1947, CHVERLAG HELVETICA CHIMICA ACTA. BASEL., pages 1869 - 1876, XP002408124 *
S. DAVID: "Contribution à l'étude de la structure du germanicol (3e partie)", BULLETIN DE LA SOCIETE CHIMIQUE DE FRANCE., 1950, FRSOCIETE FRANCAISE DE CHIMIE. PARIS., pages 169 - 172, XP002408125 *

Also Published As

Publication number Publication date
WO2006133395A2 (en) 2006-12-14

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