Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 141, Issue 8, Pages 3409-3413Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.8b13849
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Funding
- Alfred P. Sloan Foundation
- David and Lucile Packard Foundation
- Camille and Henry Dreyfus Foundation
- National Science Foundation
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An approach for the syntheses of herqulines B and C is reported that takes advantage of an L-tyrosine-derived diketopiperazine, a mycocyclosin analogue, 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. Additionally, the piperazine oxidation state is accessible via an iron-catalyzed reduction of a diketopiperazine intermediate.
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