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Synthesis of Strictosidine Analogues by Hetero‐Diels‐Alder Reaction and Their Biomimetic Transformation to Indole Alkaloids
Author(s) -
Tietze LutzF.,
Bachmann Jürgen,
Schul Wolfgang
Publication year - 1988
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.198809711
Subject(s) - indole test , knoevenagel condensation , chemistry , diastereomer , stereochemistry , transformation (genetics) , biomimetic synthesis , combinatorial chemistry , organic chemistry , biochemistry , catalysis , gene
Strictosidine, a key compound in the biosynthesis of over a thousand alkaloids , has not yet been obtained totally synthetically. The diastereomeric (easily separable) analogues of type 1 have now been prepared by tandem Knoevenagel‐hetero‐Diels‐Alder reaction (R 1 = benzyloxycarbonyl, R 2 = benzyl) and transformed into indole alkaloids.