ChemRxiv
These are preliminary reports that have not been peer-reviewed. They should not be regarded as conclusive, guide clinical practice/health-related behavior, or be reported in news media as established information. For more information, please see our FAQs.
1/1
0/0

Enantioselective Total Synthesis of (–)-Myrifabral A and B

preprint
submitted on 26.02.2020 and posted on 27.02.2020 by Tyler J. Fulton, Anthony Chen, Michael Bartberger, Brian Stoltz

A catalytic enantioselective approach to the myrioneuron alkaloids (–)-myrifabral A and (–)-myrifabral B is described. The synthesis was enabled by a palladium-catalyzed enantioselective allylic alkylation, that generates the C(10) all-carbon quaternary center. A key N-acyl iminium ion cyclization forged the cyclohexane fused tricyclic core, while vinyl boronate cross metathesis and oxidation afforded the lactol ring of (–)-myrifabral A. Adaptation of previously reported conditions allowed for the conversion of (–)-myrifabral A to (–)-myrifabral B.

Funding

NIGMS R01GM080269)

History

Email Address of Submitting Author

stoltz@caltech.edu

Institution

California Institute of Technology

Country

United States

ORCID For Submitting Author

0000-0001-9837-1528

Declaration of Conflict of Interest

no conflict of interest

Exports