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Total Synthesis of (−)‐Spirotryprostatin B
Author(s) -
Meyers Christiane,
Carreira Erick M.
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.200390192
Subject(s) - cyclopropane , oxindole , derivatization , yield (engineering) , imine , aldehyde , ring (chemistry) , chemistry , transformation (genetics) , side chain , stereochemistry , combinatorial chemistry , catalysis , organic chemistry , high performance liquid chromatography , materials science , biochemistry , polymer , metallurgy , gene
Rapid assembly of the backbone of spirotryprostatin B ( 4 ) was achieved by employing a MgI 2 ‐catalyzed ring‐expansion reaction of spiro[cyclopropane‐1,3′‐oxindole] 1 and alkynyl imine 2 to yield advanced intermediate 3 . Introduction of the prenyl side chain was accomplished by aldehyde olefination through a Julia–Kociensky reaction, a transformation that greatly facilitates late‐stage derivatization for biological studies. TIPS=triisopropylsilyl.