Synthesis of N-Acetyl-3-phenylisoserinates of Sesquiterpenoid Alcohols of Lactarius Origin

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Title:Synthesis of N-Acetyl-3-phenylisoserinates of Sesquiterpenoid Alcohols of Lactarius Origin
Creators:
Barycki, Rafał
Gumułka, Maria
Masnyk, Marek
Daniewski, Włodzimierz M.
Kobus, Mirosław
Łuczak, Mirosław
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 67, 1, pp. 75-82
Uncontrolled Keywords:Taxol, Lactarorufin, Amino acids, Sesquiterpenoids, <i>Lactarius</i> origin, Furandiol, <i>N</i>-Acetyl-3-phenylisoserine, Alcohols

Abstract

Important biological properties of Taxol <i>i.e.</i> 13-<i>N</i>-benzoyl-(2R,3S)-3-phenylisoserinate of baccatin III and also <i>N</i>-benzoyl-(2<i>R</i>,3<i>S</i>)-3-phenylisoserinates of several sesquiterpenoid alcohols of <i>Lactarius</i> origin prompted us to synthesize <i>N</i>-acetyl-3-phenylisoserinates of latter alcohols in order to check and compare their biological properties. Suitably protected phenylisoserine <strong>5</strong> when reacted with sesquiterpenoid alcohols in the presence of DCC gave appropriate esters <strong>7</strong>. These, after catalytic hydrogenation deprotection produced aminols <strong>8</strong>, which were acetylated and gave the required <i>N</i>-acetyl-3-phenylisoserinates <strong>9a</strong>-<strong>9g</strong>. <p>

Title:Synthesis of N-Acetyl-3-phenylisoserinates of Sesquiterpenoid Alcohols of Lactarius Origin
Creators:
Barycki, Rafał
Gumułka, Maria
Masnyk, Marek
Daniewski, Włodzimierz M.
Kobus, Mirosław
Łuczak, Mirosław
Uncontrolled Keywords:Taxol, Lactarorufin, Amino acids, Sesquiterpenoids, <i>Lactarius</i> origin, Furandiol, <i>N</i>-Acetyl-3-phenylisoserine, Alcohols
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:67
Number:1
Page Range:pp. 75-82
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc20020075UNSPECIFIED
ID Code:1906
Item Type:Article
Deposited On:06 Feb 2009 17:13
Last Modified:06 Feb 2009 16:13

Citation

Barycki, Rafał; Gumułka, Maria; Masnyk, Marek; Daniewski, Włodzimierz M.; Kobus, Mirosław; Łuczak, Mirosław (2002) Synthesis of N-Acetyl-3-phenylisoserinates of Sesquiterpenoid Alcohols of Lactarius Origin. Collection of Czechoslovak Chemical Communications, 67 (1). pp. 75-82. ISSN 0010-0765

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