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Enantioselective total synthesis of (−)-myrifabral A and B

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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.

Graphical abstract: Enantioselective total synthesis of (−)-myrifabral A and B

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Article information


Submitted
26 Feb 2020
Accepted
20 Apr 2020
First published
21 Apr 2020

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2020, Advance Article
Article type
Edge Article

Enantioselective total synthesis of (−)-myrifabral A and B

T. J. Fulton, A. Y. Chen, M. D. Bartberger and B. M. Stoltz, Chem. Sci., 2020, Advance Article , DOI: 10.1039/D0SC01141J

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