Issue 39, 2020

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

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

Supplementary files

Article information

Article type
Edge Article
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
Creative Commons BY license

Chem. Sci., 2020,11, 10802-10806

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

T. J. Fulton, A. Y. Chen, M. D. Bartberger and B. M. Stoltz, Chem. Sci., 2020, 11, 10802 DOI: 10.1039/D0SC01141J

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements