Functionalization of Lupane with Chromium(VI) Oxide. A Remark on the Structure of Clerodone

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Title:Functionalization of Lupane with Chromium(VI) Oxide. A Remark on the Structure of Clerodone
Creators:
Sejbal, Jan
Klinot, Jiří
Buděšínský, Miloš
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 61, 9, pp. 1371-1379
Uncontrolled Keywords:Clerodone, Lupane, Functionalization, Chromium oxide

Abstract

The reaction of lupane (<strong>1</strong>) with chromium oxide gave lup-2-en-1-one (<strong>3</strong>), lupan-12-one (<strong>2</strong>), lupan-16-one (isolated after hydride reduction as lupan-16α-ol (<strong>4</strong>)), and lup-18-en-21-one (<strong>5</strong>) in low yields. The same oxidation of 3β,28-dimethoxylupane (<strong>11</strong>) afforded no products of functionalization in non-activated positions; only products of oxidation of the 3β-methoxy group and of the oxidation cleavage of the A ring were obtained, viz. 28-methoxylupan-3β-ol formate (<strong>12</strong>), 28-methoxylupan-3-one (<strong>14</strong>), and 28-methoxy-2-norlupane-1,3-dioic anhydride (<strong>13</strong>). The structure of the compounds obtained was confirmed by their <sup>1</sup>H NMR, <sup>13</sup>C NMR, and mass spectra. The lupan-12-one (<strong>2</strong>) prepared is not identical with clerodone, whose isolation from <i>Clerodendron infortunatum</i> BHAT. was described in 1965 and to which the structure of lupan-12-one was then ascribed.

Title:Functionalization of Lupane with Chromium(VI) Oxide. A Remark on the Structure of Clerodone
Creators:
Sejbal, Jan
Klinot, Jiří
Buděšínský, Miloš
Uncontrolled Keywords:Clerodone, Lupane, Functionalization, Chromium oxide
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. 1371-1379
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19961371UNSPECIFIED
ID Code:1042
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) Functionalization of Lupane with Chromium(VI) Oxide. A Remark on the Structure of Clerodone. Collection of Czechoslovak Chemical Communications, 61 (9). pp. 1371-1379. ISSN 0010-0765

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