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Herqulines Schindler final.pdf (1.58 MB)
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Bioinspired Syntheses of Herqulines B and C from Cyclodipeptide Mycocyclosin

preprint
submitted on 24.12.2018 and posted on 26.12.2018 by Xu Zhu, Christopher C. McAtee, Corinna Schindler
A bioinspired approach for the syntheses of herqulines B and C is reported that takes advantage of an Ltyrosine-derived diketopiperazine, a mycocyclosin analog, as a synthetic precursor. The strategy relies on a series of consecutive reductions to adjust the mycocyclosin oxidation state to that observed in the herquline class of natural products. The strained and distorted L-tyrosine-based biaryl system characteristic for mycocyclosin is selectively converted to the 1,4-diketone structural motif common to the herqulines via initial hypervalent iodine-mediated dearomatization and a subsequent directed Birch reduction, enabled by an intramolecular H-source. The piperazine oxidation state is accessible in an iron-catalyzed reduction of the diketopiperazine precursor.

Funding

David and Lucile Packard Foundation, Alfred P. Sloan Foundation, Camille and Henry Dreyfus Foundation

History

Email Address of Submitting Author

corinnas@umich.edu

Institution

University of Michigan

Country

USA

ORCID For Submitting Author

0000-0003-4968-8013

Declaration of Conflict of Interest

No.

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in Journal of the American Chemical Society

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