Intramolecular N-Acyliminium Ion-Olefin Cyclization in the Synthesis of Optically Pure Isoquinoline Derivatives: Control of Stereochemistry and Application to Synthesis of Morphine Alkaloids

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Title:Intramolecular N-Acyliminium Ion-Olefin Cyclization in the Synthesis of Optically Pure Isoquinoline Derivatives: Control of Stereochemistry and Application to Synthesis of Morphine Alkaloids
Creators:
Bottari, Patricia
Endoma, Mary Ann A.
Hudlický, Tomáš
Ghiviriga, Ion
Abboud, Khalil A.
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 64, 2, pp. 203-216
Uncontrolled Keywords:Stereochemistry, Isoquinolines, Biooxidation, <i>N</i>-Acyliminium ion, Morphine, Alkaloids

Abstract

The 3-[2-(cyclohex-1-eneyl)ethyl]-[1,3]oxazoline-2,4-dione derivatives <strong>9</strong>, <strong>14</strong> and <strong>16</strong> were subjected to hydride reduction followed by acid-catalyzed olefin-<i>N</i>-acyliminium ion cyclization to afford a series of perhydroisoquinolines <strong>10</strong>, <strong>11a</strong>, <strong>11b</strong>, <strong>19a</strong>-<strong>19c</strong>, <strong>20a</strong>, <strong>20b</strong> and <strong>21</strong>. A mechanism was proposed that accounts for the observed stereoselectivity of the cyclization reactions based on the neighboring group participation by a benzoate group.

Title:Intramolecular N-Acyliminium Ion-Olefin Cyclization in the Synthesis of Optically Pure Isoquinoline Derivatives: Control of Stereochemistry and Application to Synthesis of Morphine Alkaloids
Creators:
Bottari, Patricia
Endoma, Mary Ann A.
Hudlický, Tomáš
Ghiviriga, Ion
Abboud, Khalil A.
Uncontrolled Keywords:Stereochemistry, Isoquinolines, Biooxidation, <i>N</i>-Acyliminium ion, Morphine, Alkaloids
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:64
Number:2
Page Range:pp. 203-216
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19990203UNSPECIFIED
ID Code:1470
Item Type:Article
Deposited On:06 Feb 2009 17:09
Last Modified:06 Feb 2009 16:09

Citation

Bottari, Patricia; Endoma, Mary Ann A.; Hudlický, Tomáš; Ghiviriga, Ion; Abboud, Khalil A. (1999) Intramolecular N-Acyliminium Ion-Olefin Cyclization in the Synthesis of Optically Pure Isoquinoline Derivatives: Control of Stereochemistry and Application to Synthesis of Morphine Alkaloids. Collection of Czechoslovak Chemical Communications, 64 (2). pp. 203-216. ISSN 0010-0765

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