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Cobalt versus Osmium: Control of Both trans and cis Selectivity in Construction of the EFG Rings of Pectenotoxin 4
Author(s) -
Roushanbakhti Ahria,
Liu Yifan,
Winship Paul C. M.,
Tucker Michael J.,
Akhtar Wasim M.,
Walter Daryl S.,
Wrigley Gail,
Donohoe Timothy J.
Publication year - 2017
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201708278
Subject(s) - osmium , stereoselectivity , cobalt , catalysis , chemistry , selectivity , stereochemistry , metal , combinatorial chemistry , ruthenium , organic chemistry
Catalytic oxidative cyclisation reactions have been employed for the synthesis of the E and F rings of the complex natural product target pectenotoxin 4. The choice of metal catalyst (cobalt‐ or osmium‐based) allowed for the formation of THF rings with either trans or cis stereoselectivity. Fragment union using a modified Julia reaction then enabled the synthesis of an advanced synthetic intermediate containing the EF and G rings of the target.