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Thermodynamically Controlled Stereoselective Synthesis of Geissoschizine
Author(s) -
Benson Werner,
Winterfeldt Ekkehard
Publication year - 1979
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.197908621
Subject(s) - trifluoroacetic anhydride , regioselectivity , steric effects , stereoselectivity , ring (chemistry) , chemistry , natural product , stereochemistry , organic chemistry , catalysis
Stereoconvergence is the aim of economic syntheses of natural products . Tedious saparation of the geissoschizine intermediate (3) from the by‐product (1) , which arises because of steric interactions between R and CH 3 , is avoided by hydrolyzing and cyclizing the mixture to the single dilactam (2) with trifluoroacetic anhydride. Regioselective ring opening leads only to (3) .
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