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4‐Oxo‐2‐cyclopentenyl Acetate—A Synthetic Intermediate
Author(s) -
Harre Michael,
Raddatz Peter,
Walenta Rainer,
Winterfeldt Ekkehard
Publication year - 1982
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.198204801
Subject(s) - cyclopentanone , cyclopentenone , annulation , chemistry , stereoselectivity , natural product , organic chemistry , total synthesis , enantioselective synthesis , adduct , catalysis
The present day importance of cyclopentenone derivatives in preparative organic chemistry and especially in natural product chemistry is demonstrated by the stereoselective synthesis of substituted and annelated cyclopentanone derivatives. It has been found that 4‐oxo‐2‐cyclopentenyl acetate (“4‐acetoxy‐2‐cyclopenten‐1‐one”) can be used in many reactions as a substitute for cyclopentadienone, which is itself too unstable to be isolated. A large variety of polyfunctionalized cyclopentanone derivatives, as well as carbocyclic and heterocyclic annelation products, can thus be obtained in a simple way. Various stereoselective transformations of the adducts so formed are presented, using the total synthesis of brefeldin A—a typical natural product of this series—as example. Several methods for the synthesis of 4‐oxo‐2‐cyclopentenyl acetate are outlined and, in addition, the more important methods for the enantioselective synthesis of other 4‐substituted 2‐cyclopenten‐1‐ones are discussed.