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Volumn 74, Issue 4, 1996, Pages 621-624

Asymmetric synthesis of taxol and taxotère side chains by enolate hydroxylation

Author keywords

Hydroxylation; Taxol and taxot re side chains

Indexed keywords

ESTERS; HYDROXYLATION; OXIDATION; SYNTHESIS (CHEMICAL);

EID: 0030130849     PISSN: 00084042     EISSN: None     Source Type: Journal    
DOI: 10.1139/v96-066     Document Type: Article
Times cited : (22)

References (55)
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