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Total Synthesis of Indole and Dihydroindole Alkaloids. XV . Further Chemistry of Vindoline
Author(s) -
Kutney James P.,
BunzliTrepp Ursula,
Honda Toshio,
Katsube Junki,
Worth Brian R.
Publication year - 1978
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19780610508
Subject(s) - chemistry , vindoline , potassium permanganate , indole test , electrophilic substitution , steric effects , organic chemistry , reactivity (psychology) , electrophile , medicinal chemistry , stereochemistry , medicine , alternative medicine , surgery , chemotherapy , pathology , vinblastine , catalysis
The general reactivity of various sites in the vindoline series has been investigated. The facility of electrophilic substitution at C(15) and the effect of steric crowding on reactions at C(4) are discussed. At the basic nitrogen sites, oxidations with mercuric acetate and potassium permanganate are also discussed.