Macrocyclization by Nickel‐Catalyzed, Ester‐Promoted, Epoxide–Alkyne Reductive Coupling: Total Synthesis of (−)‐Gloeosporone | Zendy

Trenkle James D. | Zendy; Jamison Timothy F. | Zendy

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Macrocyclization by Nickel‐Catalyzed, Ester‐Promoted, Epoxide–Alkyne Reductive Coupling: Total Synthesis of (−)‐Gloeosporone

Author(s) -

Trenkle James D.,

Jamison Timothy F.

Publication year - 2009

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.200902079

Subject(s) - epoxide , nickel , alkyne , total synthesis , chemistry , catalysis , yield (engineering) , phosphine , ring (chemistry) , medicinal chemistry , reductive elimination , combinatorial chemistry , stereochemistry , organic chemistry , materials science , metallurgy

Ringing the changes : The total synthesis of the title compound centers around a novel strategy that employs a nickel(0)–phosphine complex and triethyl borane in an efficient closure of a 14‐membered ring through CC bond formation (see scheme; cod=cyclooctadiene). The synthesis was accomplished in 10 steps and in approximately 9 % overall yield.

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