Premium
Total Synthesis of Indole and Dihydroindole Alkaloids. XIII . Further Chemistry of Catharanthine
Author(s) -
Kutney James P.,
Honda Toshio,
Joshua Alummoottil V.,
Lewis Norman G.,
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.19780610217
Subject(s) - chemistry , indole test , steric effects , reactivity (psychology) , stereochemistry , lactone , organic chemistry , total synthesis , medicine , alternative medicine , pathology
Further investigations on the chemistry of catharanthine have provided information, valuable in the estimation of reactivity and steric requirements of the skeleton. Specific hydroxylations at C(3), C(4) and C(18) have allowed the preparation of several derivatives including (3R, 4 R)‐3‐hydroxy‐3, 4‐dihydrocatharanthine ( 7 ); (3R,4 R)‐3, 4‐dihydroxycatharanthinic acid lactone ( 15 ); 18‐decarbomethoxy‐18‐hydroxycatharanthine ( 40 ).