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Convergent Total Synthesis of (+)‐TMC‐151C by a Vinylogous Mukaiyama Aldol Reaction and Ring‐Closing Metathesis
Author(s) -
Matsui Ryosuke,
Seto Kentaro,
Sato Yuna,
Suzuki Takahiro,
Nakazaki Atsuo,
Kobayashi Susumu
Publication year - 2011
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.201006230
Subject(s) - aldol reaction , total synthesis , ring closing metathesis , closing (real estate) , metathesis , salt metathesis reaction , computer science , chemistry , world wide web , stereochemistry , organic chemistry , political science , polymer , law , polymerization , catalysis
Two key reaction types were used for the total synthesis of the antibiotic agent (+)‐TMC‐151C: the vinylogous Mukaiyama aldol reaction and silicon‐tethered ring‐closing metathesis (RCM; see scheme). This strategy should provide efficient access to a range of related natural polyketides containing pent‐2‐ene‐1,5‐diol units.