Journal article

Synthesis of the taxol core via catalytic asymmetric 1,4-addition of an Alkylzirconium Nucleophile

Abstract:: 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 POCl3/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.

Publication status:: Published

Peer review status:: Peer reviewed

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APA Style

Wang, J. Y. J., & Fletcher, S. (2020). Synthesis of the taxol core via catalytic asymmetric 1,4-addition of an Alkylzirconium Nucleophile. Organic Letters, 22(11), 4103–4106.

MLA Style

Wang, J. YJ, and S. Fletcher. “Synthesis of the Taxol Core via Catalytic Asymmetric 1,4-Addition of an Alkylzirconium Nucleophile.” Organic Letters, vol. 22, no. 11, American Chemical Society, 2020, pp. 4103–06.

Chicago Style

Wang, JYJ, and S Fletcher. 2020. “Synthesis of the Taxol Core via Catalytic Asymmetric 1,4-Addition of an Alkylzirconium Nucleophile.” Organic Letters 22 (11): 4103–6.
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Files:: WangFletcherAAM2020.pdf

(Preview, Accepted manuscript, 456.1KB, Terms of use)

Publisher copy:: 10.1021/acs.orglett.0c01165

Authors

+ Wang, JYJ More by this author

Institution:: University of Oxford
Division:: MPLS
Department:: Chemistry
Sub department:: Chemistry Research Laboratory
Role:: Author
ORCID:: 0000-0002-6180-7452

+ Fletcher, S More by this author

Institution:: University of Oxford
Division:: MPLS
Department:: Chemistry
Sub department:: Organic Chemistry
Role:: Author

+ Engineering & Physical Sciences Research Council More from this funder

Grant:: EP/H003711/1

Publisher:: American Chemical Society
Journal:: Organic Letters More from this journal
Volume:: 22
Issue:: 11
Pages:: 4103–4106
Publication date:: 2020-05-12
Acceptance date:: 2020-05-06
DOI:: 10.1021/acs.orglett.0c01165
EISSN:: 1523-7052
ISSN:: 1523-7052

Language:: English
Keywords:: FFR
Pubs id:: 1103233
Local pid:: pubs:1103233
Deposit date:: 2020-05-06

Terms of use

Copyright holder:: American Chemical Society
Copyright date:: 2020
Rights statement:: © 2020 American Chemical Society
Notes:: This is the accepted manuscript version of the article. The final version is available from ACS Publications at: https://doi.org/10.1021/acs.orglett.0c01165

Licence:: Terms and Conditions of Use for Oxford University Research Archive

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