Reversing the Reactivity of Carbonyl Functions with Phosphonium Salts: Enantioselective Total Synthesis of (+)‐Centrolobine | Zendy

Fujioka Hiromichi | Zendy; Yahata Kenzo | Zendy; Kubo Ozora | Zendy; Sawama Yoshinari | Zendy; Hamada Tomohito | Zendy; Maegawa Tomohiro | Zendy

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Reversing the Reactivity of Carbonyl Functions with Phosphonium Salts: Enantioselective Total Synthesis of (+)‐Centrolobine

Author(s) -

Fujioka Hiromichi,

Yahata Kenzo,

Kubo Ozora,

Sawama Yoshinari,

Hamada Tomohito,

Maegawa Tomohiro

Publication year - 2011

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.201106046

Subject(s) - enantioselective synthesis , phosphonium , alkylation , trimethylsilyl , chemistry , reactivity (psychology) , yield (engineering) , total synthesis , organic chemistry , combinatorial chemistry , medicinal chemistry , catalysis , materials science , medicine , alternative medicine , pathology , metallurgy

Step saver : Carbonyl groups with lower reactivities can be transformed in the presence of more reactive ones by treatment with PPh 3 (or PEt 3 ) and TMSOTf prior to the reaction (see scheme; TMS=trimethylsilyl, Tf=trifluoromethanesulfonyl). This methodology can be applied to reduction and alkylation reactions, and enabled the short asymmetric total synthesis of (+)‐centrolobine with the highest overall yield reported to date.

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