A Hetero Diels-Alder Access to (Z)-Zeatin and (Z)-Isozeatin

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Title:A Hetero Diels-Alder Access to (Z)-Zeatin and (Z)-Isozeatin
Creators:
Tolman, Vladimír
Hanuš, Jan
Sedmera, Petr
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 64, 4, pp. 696-702
Uncontrolled Keywords:Diels-Alder reaction, Cytokinins, Purines, Cycloadditions, Nitrosoformates, Zeatin, 3,4-Dihydrooxazines, Diene synthesis

Abstract

(<i>Z</i>)-6-(4-Hydroxy-3-methylbut-2-en-1-ylamino)purine, (<i>Z</i>)-zeatin, and the isomeric (<i>Z</i>)-isozeatin, both free from the <i>E</i> isomers, were prepared using the cycloaddition of the <i>in situ</i> generated <i>tert</i>-butyl nitrosoformate on isoprene. A mixture of <i>tert</i>-butyl 5(and 4)-methyl-3,6-dihydro-2<i>H</i>-1,2-oxazine-2-carboxylates thus formed was deprotected and reductively cleaved to (<i>Z</i>)-4-amino-2(and 3)-methylbut-2-en-1-ols, which were chromatographically separated and finally alkylated with 6-chloropurine to give the title compounds. <p>

Title:A Hetero Diels-Alder Access to (Z)-Zeatin and (Z)-Isozeatin
Creators:
Tolman, Vladimír
Hanuš, Jan
Sedmera, Petr
Uncontrolled Keywords:Diels-Alder reaction, Cytokinins, Purines, Cycloadditions, Nitrosoformates, Zeatin, 3,4-Dihydrooxazines, Diene synthesis
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:4
Page Range:pp. 696-702
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19990696UNSPECIFIED
ID Code:1509
Item Type:Article
Deposited On:06 Feb 2009 17:10
Last Modified:06 Feb 2009 16:10

Citation

Tolman, Vladimír; Hanuš, Jan; Sedmera, Petr (1999) A Hetero Diels-Alder Access to (Z)-Zeatin and (Z)-Isozeatin. Collection of Czechoslovak Chemical Communications, 64 (4). pp. 696-702. ISSN 0010-0765

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