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The Second Total Synthesis of Diazonamide A
Author(s) -
Nicolaou K. C.,
Bheema Rao Paraselli,
Hao Junliang,
Reddy Mali Venkat,
Rassias Gerasimos,
Huang Xianhai,
Chen David Y.K.,
Snyder Scott A.
Publication year - 2003
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.200351112
Subject(s) - total synthesis , oxindole , indoline , natural product , cascade , sequence (biology) , stereochemistry , closing (real estate) , chemistry , combinatorial chemistry , ring (chemistry) , organic chemistry , biochemistry , business , chromatography , catalysis , finance
The uniquely woven , highly strained molecular architecture and the potent antitumor activity of diazonamide A ( 1 ) make this natural product an attractive synthetic target. The key steps in this total synthesis of 1 include a novel SmI 2 ‐induced ring‐closing cascade sequence and an unusual oxidation of an indoline to an oxindole in the presence of Pd(OH) 2 /C.