Published October 21, 2020
| Supplemental Material + Submitted + Published
Journal Article
Open
Enantioselective Total Synthesis of (–)-Myrifabral A and B
Chicago
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Abstract
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.
Additional Information
© 2020 The Royal Society of Chemistry. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. All publication charges for this article have been paid for by the Royal Society of Chemistry. Submitted 26 Feb 2020; Accepted 20 Apr 2020; First published 21 Apr 2020. We thank NIH-NIGMS (R01GM080269) and Caltech for financial support. Dr Scott Virgil (Caltech) is thanked for instrumentation and SFC assistance. We thank Dr David Vander Velde (Caltech) for NMR expertise, and Dr Mona Shahgholi (Caltech) and Naseem Torian (Caltech) for mass spectrometry assistance. There are no conflicts to declare.Attached Files
Published - d0sc01141j.pdf
Submitted - Enantioselective_Total_Synthesis_of____-Myrifabral_A_and_B_v1.pdf
Supplemental Material - d0sc01141j1_si.pdf
Files
Enantioselective_Total_Synthesis_of____-Myrifabral_A_and_B_v1.pdf
Additional details
- PMCID
- PMC8162428
- Eprint ID
- 101714
- Resolver ID
- CaltechAUTHORS:20200304-153439734
- NIH
- R01GM080269
- Caltech
- Created
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2020-03-04Created from EPrint's datestamp field
- Updated
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2021-06-07Created from EPrint's last_modified field