Oleanane Triterpenoids Functionalized at C-25 and C-26

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Title:Oleanane Triterpenoids Functionalized at C-25 and C-26
Creators:
Sejbal, Jan
Klinot, Jiří
Buděšínský, Miloš
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 61, 9, pp. 1360-1370
Uncontrolled Keywords:Oleanane, Triterpenoids, Oximes, Functionalization

Abstract

Reaction of 25-oximino-19β,28-epoxy-18α-oleanan-2β-ol (<strong>4</strong>) with nitrous acid afforded hemiacetal <strong>22</strong> ((25<i>S</i>)-2β,25;19β,28-diepoxy-18α-oleanan-25-ol). Functionalization of 19β,28-epoxy-18α-oleanan-2β-ol (<strong>1</strong>) with lead(IV) acetate gave 2β,25;19β,28-diepoxy-18α-oleanane (<strong>31</strong>). A series of derivatives with an oxygen functionality at position 25 has been prepared by modification of the functional groups in compounds <strong>22</strong> and <strong>31</strong>. 26-Oximino-19β,28-epoxy-18α-oleanan-2β-ol (<strong>7</strong>) on reaction with nitrous acid afforded the corresponding nitrimine <strong>10</strong> which could not be converted into derivatives with an oxygen group at C-26: all the attempted preparations led invariably to compounds containing a nitrile group in position 8β. The nitrile groups in positions 10β and 8β appeared to be extremely unreactive.

Title:Oleanane Triterpenoids Functionalized at C-25 and C-26
Creators:
Sejbal, Jan
Klinot, Jiří
Buděšínský, Miloš
Uncontrolled Keywords:Oleanane, Triterpenoids, Oximes, Functionalization
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:61
Number:9
Page Range:pp. 1360-1370
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19961360UNSPECIFIED
ID Code:1041
Item Type:Article
Deposited On:06 Feb 2009 17:06
Last Modified:06 Feb 2009 16:06

Citation

Sejbal, Jan; Klinot, Jiří; Buděšínský, Miloš (1996) Oleanane Triterpenoids Functionalized at C-25 and C-26. Collection of Czechoslovak Chemical Communications, 61 (9). pp. 1360-1370. ISSN 0010-0765

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