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The Reversible Nicholas Reaction in the Synthesis of Highly Symmetric Natural‐Product‐Based Macrocycles
Author(s) -
de la Torre María C.,
Asenjo María,
RamírezLópez Pedro,
Sierra Miguel A.
Publication year - 2015
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/ejoc.201403541
Subject(s) - chemistry , natural product , moiety , stereochemistry , propargyl , adduct , sequence (biology) , alcohol , propargyl alcohol , benzene , template , combinatorial chemistry , organic chemistry , catalysis , nanotechnology , biochemistry , materials science
Two different approaches to highly symmetric macrocycles by reversible Nicholas reactions have been developed. The first sequence uses a bis[Co 2 (CO) 6 ] complex derived from a double propargylic alcohol supporting two natural product moieties. The reactions with BF 3 · OEt 2 and different benzene dimethanols yielded either (1:1) or (2:2) adducts, depending essentially on the nature of the tether joining both Co clusters. Alternatively, the Nicholas reactions of Co‐complexed propargyl alcohol templates with one steroid and one monoterpene fragment as well as one aromatic terminus containing an alcohol moiety yielded the corresponding macrocycles derived from self‐dimerization. Both routes to macrocycles are complementary and efficiently produce sophisticated natural‐product‐containing structures.