Synthesis of the Taxol Core via Catalytic Asymmetric 1,4-Addition of an Alkylzirconium Nucleophile | Zendy

Jiao Yu J. Wang | Zendy; Stephen P. Fletcher | Zendy

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Synthesis of the Taxol Core via Catalytic Asymmetric 1,4-Addition of an Alkylzirconium Nucleophile

Author(s) -

Jiao Yu J. Wang,

Stephen P. Fletcher

Publication year - 2020

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.0c01165

Subject(s) - chemistry , nucleophile , yield (engineering) , allylic rearrangement , conjugate , intramolecular force , catalysis , trapping , medicinal chemistry , combinatorial chemistry , stereochemistry , organic chemistry , mathematical analysis , ecology , materials science , mathematics , metallurgy , biology

The Taxol core was prepared in five steps via a key copper-catalyzed asymmetric conjugate addition trapping sequence. The use of a bromodiene-derived alkylzirconium nucleophile followed by trapping with POCl 3 /DMF gave a highly functionalized intermediate featuring a quaternary center in 69% yield with 92% ee. After 1,2-addition, Suzuki-Miyaura cross-coupling, allylic oxidation, and a type II intramolecular Diels-Alder reaction, the taxol core was obtained in 11% overall yield with 92% ee.

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