Cobalt versus Osmium: Control of Both trans and cis Selectivity in Construction of the EFG Rings of Pectenotoxin4

Catalytic oxidative cyclisation reactions have been employed for the synthesis of the E and F rings of the complex natural product target pectenotoxin4. The choice of metal catalyst (cobalt- or osmium-based) allowed for the formation of THF rings with either trans or cis stereoselectivity. Fragment...

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Bibliographic Details
Published inAngewandte Chemie Vol. 129; no. 47; p. 15079
Main Authors Roushanbakhti, Ahria, Liu, Yifan, Winship, Paul C M, Tucker, Michael J, Akhtar, Wasim M, Walter, Daryl S, Wrigley, Gail, Donohoe, Timothy J
Format Journal Article
LanguageGerman
Published Weinheim Wiley Subscription Services, Inc 20.11.2017
Subjects
Catalysis
Chemical synthesis
Chemistry
Cobalt
Osmium
Selectivity
Stereoselectivity
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Summary:Catalytic oxidative cyclisation reactions have been employed for the synthesis of the E and F rings of the complex natural product target pectenotoxin4. 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.
ISSN:0044-8249
1521-3757
DOI:10.1002/ange.201708278