Premium
Total Synthesis of Indole and Dihydroindole Alkaloids. VIII . Studies on the synthesis of bisindole alkaloids in the vinblastine‐vincristine series. The chloroindolenine approach
Author(s) -
Kutney James P.,
Beck John,
Bylsma Feike,
Cook James,
Cretney Walter J.,
Fuji Kaoru,
Imhof René,
Treasurywala Adi M.
Publication year - 1975
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.19750580622
Subject(s) - vindoline , chemistry , vinblastine , indole test , stereochemistry , total synthesis , vinca , alkaloid , pharmacology , surgery , chemotherapy , medicine
Studies on the syntheses of 18′‐epi‐4′‐deoxo‐4′‐epivinblastine (IX, R = CO 2 CH 3 ; R 1 = H), 18′‐decarbomethoxy‐18′‐epi‐4′‐deoxo‐4′‐epivinblastine (IX, R = R 1 = H) and related analogues are described. The synthetic method employs a coupling reaction involving chloroindolenine derivatives of the cleavamine series (for example, III) with vindoline (V) under acidic conditions. The complete structures, including absolute configuration, of the resulting dimers are established by a combination of chemical and spectroscopic techniques, including X‐ray analysis.