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Palladium‐Catalyzed Allylic Substitution for the Synthesis of Pericosines
Author(s) -
Chung ChengYu,
Angamuthu Venkatachalam,
Li LongShiang,
Hou DuenRen
Publication year - 2016
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201600355
Subject(s) - chemistry , allylic rearrangement , palladium , catalysis , tsuji–trost reaction , adduct , substitution reaction , metathesis , ring closing metathesis , sn2 reaction , medicinal chemistry , organic chemistry , stereochemistry , combinatorial chemistry , polymerization , polymer
A sequence of vinylalumination of α‐substituted aldehydes, ring‐closing metathesis (RCM), and palladium‐catalyzed allylic substitution was utilized to prepare the biologically active natural products, pericosines, from d ‐ribose. The anti ‐adduct of vinylalumination was transformed into pericosine A after RCM, removal of the 4‐methoxybenzyl protecting group, and chlorination. The diacetate of the anti ‐adduct was converted to pericosine C after the palladium‐catalyzed, S N 2′‐type, allylic substitution. However, an unexpected dimeric product was generated in utilizing this approach to prepare pericosine E.