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

Fulton, Tyler J.; Chen, Anthony Y.; Bartberger, Michael D.; Stoltz, Brian M.

doi:10.1039/d0sc01141j

Cited by 13 publications

(9 citation statements)

References 29 publications

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“…A very recent example from the Stoltz group on the use of Pd-catalyzed DAAA as a key transformation in total synthesis can be found in the asymmetric synthesis of the Myrioneuron alkaloids (−)-myrifabral A and B ( Scheme 267 ). 667 The use of the Pd/( S )- L122 catalyst generated the C(10) all-carbon quaternary center (from the key compound 253 ). The synthesis of myrifabral A was accomplished from 253 in 66% overall yield followed by diastereoselective N -acyl iminium cyclization, cross metathesis and subsequent oxidation.…”

Section: Asymmetric Decarboxylative Allylic Substitutionmentioning

confidence: 99%

Recent Advances in Enantioselective Pd-Catalyzed Allylic Substitution: From Design to Applications

Pàmies

Margalef

Cañellas³

et al. 2021

Chem. Rev.

382

202

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This Review compiles the evolution, mechanistic understanding, and more recent advances in enantioselective Pd-catalyzed allylic substitution and decarboxylative and oxidative allylic substitutions. For each reaction, the catalytic data, as well as examples of their application to the synthesis of more complex molecules, are collected. Sections in which we discuss key mechanistic aspects for high selectivity and a comparison with other metals (with advantages and disadvantages) are also included. For Pd-catalyzed asymmetric allylic substitution, the catalytic data are grouped according to the type of nucleophile employed. Because of the prominent position of the use of stabilized carbon nucleophiles and heteronucleophiles, many chiral ligands have been developed. To better compare the results, they are presented grouped by ligand types. Pd-catalyzed asymmetric decarboxylative reactions are mainly promoted by PHOX or Trost ligands, which justifies organizing this section in chronological order. For asymmetric oxidative allylic substitution the results are grouped according to the type of nucleophile used.

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Section: Asymmetric Decarboxylative Allylic Substitutionmentioning

confidence: 99%

Recent Advances in Enantioselective Pd-Catalyzed Allylic Substitution: From Design to Applications

Pàmies

Margalef

Cañellas³

et al. 2021

Chem. Rev.

382

202

View full text Add to dashboard Cite

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“…This intermediate can then undergo an intramolecular Mannich-type addition promoted by Lewis acid BF 3 .OEt 2 to produce in gram scale a common precursor 32 in 89 % yield. This compound could be converted after several other steps to both (À )-α-myrifabrals A and B [24] (Scheme 6).…”

Section: Cyclization Events Using Masked N-acyliminium Ionsmentioning

confidence: 99%

Cyclization Strategies Using Imide Derivatives for the Synthesis of Polycyclic Nitrogen‐Containing Compounds

2022

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Cyclization strategies employing imides and their derivatives have attracted the attention of several organic chemists interested in synthesizing polycyclic alkaloids. Numerous strategies have been developed, mostly focused on i) the use of masked iminium ions, ii) addition of weak nucleophiles onto the carbonyl group of the imide being activated by a Lewis or Brønsted acid, iii) addition of strong nucleophiles onto the imide carbonyl, iv) radical-based processes and v) miscellaneous methods. This review is not comprehensive. It aims to provide the reader with a selection of representative synthetic strategies available in the area up to date.

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“…In 2020, Stoltz group described the first enantioselective total synthesis of Myrioneuron alkaloids (-)-myrifabral A and B by using Pd-catalyzed DAAA to construct the all-carbon quaternary stereocenter with (S)-(CF3)3-t-BuPHOX L3 as chiral ligand (Scheme 30). 70 Pd-catalyzed DAAA was performed at 10g scale, affording the desired product in 94% yield and 88% ee. The following transformation of ketone protection and glutarimide…”

Section: Scheme 29 Total Synthesis Of (+)-Aspidospermidine By Changmentioning

confidence: 99%

“…In 2020, the Stoltz group described the first enantioselective total synthesis of Myrioneuron alkaloids (-)-myrifabral A and B by using Pd-catalyzed DAAA to construct the all-carbon quaternary stereocenter with (S)-(CF 3 ) 3 -t-Bu-PHOX L3 as chiral ligand (Scheme 30). 68…”

Section: Scheme 26 Formal Synthesis Of (-)-Platencin By Stoltzmentioning

confidence: 99%

Recent Advances in the Construction of Quaternary Stereocenters via Palladium-Catalyzed Decarboxylative Asymmetric Allylic Alkylation

Zhang

Liu

et al. 2021

Synthesis

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Palladium catalyzed decarboxylative asymmetric allylic alkylation (DAAA) provides an efficient and powerful strategy to construct quaternary stereocenters which are widely present in biologically active natural products and approved drugs. In this short review, we summarize recent developments (since 2018) in the facile synthesis of quaternary stereocenters via DAAA methods. Several representative examples by using DAAA strategy for total synthesis of complex natural products further demonstrate its synthetic potential in the realm of organic and medicinal chemistry

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

Abstract: A catalytic enantioselective approach to the Myrioneuron alkaloids (−)-myrifabral A and (−)-myrifabral B is described.

Cited by 13 publications

References 29 publications

Recent Advances in Enantioselective Pd-Catalyzed Allylic Substitution: From Design to Applications

Recent Advances in Enantioselective Pd-Catalyzed Allylic Substitution: From Design to Applications

Cyclization Strategies Using Imide Derivatives for the Synthesis of Polycyclic Nitrogen‐Containing Compounds

Recent Advances in the Construction of Quaternary Stereocenters via Palladium-Catalyzed Decarboxylative Asymmetric Allylic Alkylation

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