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Gardenamide A from Rothmannia urcelliformis (Rubiaceae) − Isolation, Absolute Stereostructure, and Biomimetic Synthesis from Genipine
Author(s) -
Bringmann Gerhard,
Hamm Andreas,
Kraus Jürgen,
Ochse Michael,
Noureldeen Amal,
Jumbam Dennis N.
Publication year - 2001
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200105)2001:10<1983::aid-ejoc1983>3.0.co;2-g
Subject(s) - rubiaceae , chemistry , iridoid , stereochemistry , absolute configuration , biomimetic synthesis , chirality (physics) , total synthesis , botany , glycoside , physics , biology , nambu–jona lasinio model , chiral symmetry breaking , quantum mechanics , quark
The iridoid alkaloid gardenamide A ( 3 ) was isolated from the phytochemically uninvestigated East African Rubiaceae species Rothmannia urcelliformis (Hiern) Bullock. Its absolute stereostructure was determined by quantum chemical CD calculations, which constitutes the first application of this useful chiroptical tool within the class of iridoids. An additional stereochemical proof succeeded by its biomimetic partial synthesis starting from the well‐known nitrogen‐free iridoid genipine ( 1 ).