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Efficient Synthesis of Six‐Membered Ring D Analogues of the Pentacyclic Alkaloid Cephalotaxine by Two Palladium‐Catalyzed Reactions
Author(s) -
Tietze Lutz F.,
Schirok Hartmut,
Wöhrmann Michael,
Schrader Klaus
Publication year - 2000
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200007)2000:13<2433::aid-ejoc2433>3.0.co;2-g
Subject(s) - chemistry , amination , intramolecular force , palladium , acylation , ring (chemistry) , alkylation , catalysis , heck reaction , allylic rearrangement , tsuji–trost reaction , stereochemistry , medicinal chemistry , organic chemistry
D‐ homo ‐Cephalotaxine analogues 19 and 23 have been prepared by intramolecular Heck reactions of 12 and 22 . The substrates 12 and 22 were obtained by alkylation and acylation, respectively, of the spirocyclic amines 17 , which, in turn, were generated by intramolecular palladium‐catalyzed allylic amination.