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Volumn 56, Issue 9, 2000, Pages 1181-1192

Novel dimeric taxoids via highly regio- and stereospecific Diels-Alder cycloadditions of taxinine B and taxicine I derivatives

Author keywords

Biologically active compounds; Diels Alder reactions; Regiospecificity; Stereospecificity; Taxoids

Indexed keywords

ALCOHOL; ALKADIENE; ALUMINUM DERIVATIVE; LACTONE DERIVATIVE; TAXININE; TAXOID;

EID: 0034712162     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(00)00007-7     Document Type: Article
Times cited : (5)

References (54)
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    • Paclitaxel is being produced commercially by direct isolation from Taxus species by several companies, such as Hauser Chemical Research, Inc., Boulder, CO; NaPro Bio Therapeutics, Inc., Boulder, CO; and Beijing Union Pharm. Plant, Institute of Materia Medica, Chinese Academy of Medical Sciences, Beijing, China.
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    • Key NOE correlations of 8 and 9 are as follows:
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    • Calculations were performed on Macintosh using CS Chem 3D Pro. 3.2. in Tohoku University, Japan
    • Calculations were performed on Macintosh using CS Chem 3D Pro. 3.2. in Tohoku University, Japan.
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    • 7,22) was observed in the resonances at δ 2.98 (dd) and δ 3.17 (dd) assigned to coupling between the bridgehead proton H-7 and the exo proton (H-22) in the bicyclo[2.2.]octene skeleton of 17. These observations infer that 16 possesses exo stereochemistry whereas 17 possesses endo stereochemistry. This tentative assignment was further confirmed by NOE experiments which demonstrated a pattern of NOE which was consistent only with exo (H-22) stereochemistry. The key NOESY correlations of exo-16 and endo-17 as follows (500 MHz, CDCl3):
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