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. 2020 Apr 21;11(39):10802-10806.
doi: 10.1039/d0sc01141j.

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

Tyler J Fulton  1 , Anthony Y Chen  1 , Michael D Bartberger  2 , Brian M Stoltz  1
Affiliations

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

Tyler J Fulton et al. Chem Sci. .

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.

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Conflict of interest statement

There are no conflicts to declare.

Figures

Fig. 1
Fig. 1. Representative Myrioneuron alkaloids.
Scheme 1
Scheme 1. Retrosynthetic analysis of (−)-myrifabral A.
Scheme 2
Scheme 2. Initial synthesis of glutarimide 8.
Scheme 3
Scheme 3. Enantioselective synthesis of tricyclic lactam 6.
Scheme 4
Scheme 4. End game for (−)-myrifabral A.
Scheme 5
Scheme 5. Synthesis of (−)-myrifabral B.
See this image and copyright information in PMC

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