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Total Synthesis of the Tubulin Inhibitor WF‐1360F Based on Macrocycle Formation through Ring‐Closing Alkyne Metathesis
Author(s) -
Neuhaus Christian M.,
Liniger Marc,
Stieger Martin,
Altmann KarlHeinz
Publication year - 2013
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.201300576
Subject(s) - alkyne , total synthesis , ring closing metathesis , chemistry , moiety , stereochemistry , natural product , ring (chemistry) , salt metathesis reaction , metathesis , combinatorial chemistry , organic chemistry , catalysis , polymerization , polymer
Key steps in this total synthesis of the antimitotic natural product WF‐1360F ( 3 ) include the formation of the macrocycle through ring‐closing alkyne metathesis and the subsequent conversion of the ensuing alkyne moiety into an E ‐configured double bond. As illustrated by the synthesis of 4 , the macrocyclic vinyl iodide 2 can also serve as a common precursor for the synthesis of side‐chain‐modified rhizoxin analogues (see scheme; TIPS=triisopropylsilyl).