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Palladium‐Catalyzed Ene‐Type Cyclizations of Terpenoid 1,6‐Enynes
Author(s) -
Knierzinger Andreas,
Grieder Alfred,
Schönholzer Peter
Publication year - 1991
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19910740308
Subject(s) - cyclopentane , chemistry , palladium , ene reaction , catalysis , yield (engineering) , terpenoid , context (archaeology) , type (biology) , stereochemistry , organic chemistry , medicinal chemistry , paleontology , ecology , materials science , metallurgy , biology
Abstract Palladium‐catalyzed ene‐type cyclizations of 1,6‐enynes 2 yield methylidene‐cyclopentane derivatives 3 . Removal of protecting groups from 3 furnishes the diols 4 and 5 , whose configurations were established by a combination of X‐ray and 1 H‐NMR techniques. The predominant formation of isomers 4 is discussed in the context of two alternative hypothetical mechanisms previously proposed for this type of cyclization.