WO2006133395A3 - Stereoselective reduction of triterpenones - Google Patents

Stereoselective reduction of triterpenones Download PDF

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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
Application number
PCT/US2006/022422
Other languages
French (fr)
Other versions
WO2006133395A2 (en
Inventor
Pavel A Krasutsky
Kalyan Munshi
Original Assignee
Univ Minnesota
Pavel A Krasutsky
Kalyan Munshi
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 Univ Minnesota, Pavel A Krasutsky, Kalyan Munshi filed Critical Univ Minnesota
Publication of WO2006133395A2 publication Critical patent/WO2006133395A2/en
Publication of WO2006133395A3 publication Critical patent/WO2006133395A3/en

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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

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  • 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 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 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
WO2009073818A1 (en) * 2007-12-04 2009-06-11 Myriad Genetics, 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
EP3735274A1 (en) 2018-01-04 2020-11-11 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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