Synthesis of N-Acetyl-3-phenylisoserinates of Sesquiterpenoid Alcohols of Lactarius Origin
- 1 January 2002
- journal article
- Published by Institute of Organic Chemistry & Biochemistry in Collection of Czechoslovak Chemical Communications
- Vol. 67 (1) , 75-82
- https://doi.org/10.1135/cccc20020075
Abstract
Important biological properties of Taxol i.e. 13-N-benzoyl-(2R,3S)-3-phenylisoserinate of baccatin III and also N-benzoyl-(2R,3S)-3-phenylisoserinates of several sesquiterpenoid alcohols of Lactarius origin prompted us to synthesize N-acetyl-3-phenylisoserinates of latter alcohols in order to check and compare their biological properties. Suitably protected phenylisoserine 5 when reacted with sesquiterpenoid alcohols in the presence of DCC gave appropriate esters 7. These, after catalytic hydrogenation deprotection produced aminols 8, which were acetylated and gave the required N-acetyl-3-phenylisoserinates 9a-9g.Keywords
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