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Enantioselective Synthesis of Arglabin
Author(s) -
Kalidindi Srinivas,
Jeong Won Boo,
Schall Andreas,
Bandichhor Rakeshwar,
Nosse Bernd,
Reiser Oliver
Publication year - 2007
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200701584
Subject(s) - enantioselective synthesis , cyclopropanation , metathesis , stereochemistry , stereoselectivity , ring closing metathesis , ring (chemistry) , natural product , chemistry , combinatorial chemistry , catalysis , organic chemistry , polymerization , polymer
Closing the ring : The first enantioselective synthesis of the guanianolide natural product arglabin and its dimethylamino adduct, which shows promising results in the treatment of various tumors, has been achieved. Key steps include a Cu I ‐catalyzed asymmetric cyclopropanation, a stereoselective Sakurai allylation with a retroaldol/lactonization cascade, and a second Sakurai allylation with ring‐closing metathesis (RCM).