Functionalization of Lupane-3β,28-diyl Diacetate with Chromium(VI) Oxide. Part 2

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Title:Functionalization of Lupane-3β,28-diyl Diacetate with Chromium(VI) Oxide. Part 2
Creators:
Sejbal, Jan
Klinot, Jiří
Buděšínský, Miloš
Protiva, Jiří
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 62, 12, pp. 1905-1918
Uncontrolled Keywords:Triterpenes, Triterpenoids, Chromium (VI) oxide, Functionalization, Oxidation, Lupane derivatives

Abstract

Oxidation of lupane-3β,28-diyl diacetate (<strong>1</strong>) with chromium trioxide was reported already earlier to give small amounts of products functionalized in position 19β and 11 (19β-hydroxylupane-3β,28-diyl diacetate (<strong>3</strong>) and 11-oxolupane-3β,28-diyl diacetate (<strong>6</strong>)), together with products of subsequent oxidation, 21-oxolup-18-ene-3β,28-diyl diacetate (<strong>4</strong>) and anhydride (<strong>5</strong>). Now we identified further products, arising by functionalization in positions 12, 16 and 21 (12-hydroxy-11-oxolup-12-ene-3β,28-diyl diacetate (<strong>8</strong>), 12-oxolupane-3β,28-diyl diacetate (<strong>9</strong>), 11-oxolup-12-ene-3β,28-diyl diacetate (<strong>17</strong>), 21-oxolupane-3β,28-diyl diacetate (<strong>20</strong>) and 16-oxolupane-3β,28-diyl diacetate (<strong>22</strong>)), either as such or after conversion into other derivatives. The obtained compounds were further transformed and structure of the prepared derivatives was confirmed by <sup>1</sup>H NMR, <sup>13</sup>C NMR and mass spectroscopy.

Title:Functionalization of Lupane-3β,28-diyl Diacetate with Chromium(VI) Oxide. Part 2
Creators:
Sejbal, Jan
Klinot, Jiří
Buděšínský, Miloš
Protiva, Jiří
Uncontrolled Keywords:Triterpenes, Triterpenoids, Chromium (VI) oxide, Functionalization, Oxidation, Lupane derivatives
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:62
Number:12
Page Range:pp. 1905-1918
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19971905UNSPECIFIED
ID Code:1264
Item Type:Article
Deposited On:06 Feb 2009 17:08
Last Modified:06 Feb 2009 16:08

Citation

Sejbal, Jan; Klinot, Jiří; Buděšínský, Miloš; Protiva, Jiří (1997) Functionalization of Lupane-3β,28-diyl Diacetate with Chromium(VI) Oxide. Part 2. Collection of Czechoslovak Chemical Communications, 62 (12). pp. 1905-1918. ISSN 0010-0765

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