A Stereoselective Arylative-Cyclopropanation Process

Coulibali, Siomenan; Deruer, Elsa; Godin, Elizabeth; Canesi, Sylvain

doi:10.1021/acs.orglett.7b00248

Cited by 21 publications

(8 citation statements)

References 50 publications

(17 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Furthermore, the indoline precursor was installed with the aluminum salt of 2-iodoaniline to generate the amide in 87% yield (Scheme ). Subsequent activation with the hypervalent iodine reagent (diacetoxyiodo)benzene or phenyliodine diacetate under Kita’s conditions led to dienone 11 in 89% yield. At this stage, we developed a diastereoselective aza-Michael-enol ether tandem process promoted by tert -butyldimethylsilyl trifluoromethanesulfonate (TBSOTf) and triethylamine to produce enol ether 13 .…”

Section: Resultsmentioning

confidence: 99%

Common Strategy for the Synthesis of Some Strychnos Indole Alkaloids

et al. 2020

Self Cite

View full text Add to dashboard Cite

Indole alkaloids are important natural compounds with interesting bio-activities that can be found in various species belonging to the Amaryllidaceae, Apocynaceae, or Strychnaceae families. Although these compounds have different connections, substituents, and functionalities, their main core can be produced via the formation of a common functionalized tetracyclic subunit, which is rapidly obtained by an oxidative de-aromatization process mediated by a hypervalent iodine reagent from an inexpensive phenol containing a lactate moiety as the chiral auxiliary. A subsequent stereoselective aza-Michael addition and an intramolecular Heck-type reaction lead to the formation of a common key intermediate. This approach provides a solid foundation for the further elaborations of several natural products. The asymmetric syntheses of (−)-strychnopivotine and the polycyclic main cores of (−)-strychnosplendine, (+)-isosplendine, and (+)-malagashanol, three other indole alkaloids, are reported.

show abstract

Section: Resultsmentioning

confidence: 99%

Common Strategy for the Synthesis of Some Strychnos Indole Alkaloids

et al. 2020

Self Cite

View full text Add to dashboard Cite

show abstract

“…In the process of extending this approach to bromoenones, we developed an arylation-cyclopropanation process, 60 which was used to diastereoselectively synthesize 170, Scheme 54.…”

Section: Scheme 53 Indole Formationmentioning

confidence: 99%

Rapid Formation of Advanced Scaffolds from Phenols and Anilines

Canesi

2018

Synlett

Self Cite

View full text Add to dashboard Cite

This article is an account of our efforts over the last decade to functionalize phenols and anilines at any position and to use these compounds to generate substituted aromatic systems and advanced unsaturated cyclohexanone moieties, enabling the rapid formation of complex structures. Total syntheses of numerous natural products involving such intermediates were achieved.1 Introduction2 ortho-Functionalization of Phenols and Aniline Derivatives Mediated by Iodanes (III) and Synthesis of Panacene2.1 Cross-Coupling with Aniline Derivatives2.2 Dearomative Cycloaddition of Arenes and Heteroarenes2.3 Total Synthesis of Panacene3 meta-Functionalization of Aniline Derivatives and Synthesis of Erysotramidine3.1 meta-Functionalization of Aniline Derivatives3.2 Total Synthesis of Erysotramidine4 para-Functionalization of Phenols and Applications in Total Synthesis4.1 Bimolecular Approach Mediated by Protecting Groups4.2 ipso-Rearrangement4.3 Oxidative Alkyl Shift4.4 Oxidative Prins-Pinacol Rearrangement4.5 Oxidative Prins-Type Reaction4.6 Total Synthesis of (–)-Fortucine4.7 Total Synthesis of Isostrychnine4.8 Total Synthesis of (–)-Strychnopivotine5 Development of a Functional Protecting Group

show abstract

“…6 In addition, they have reported a Michael−Smiles ring-closure cascade process to construct arylated cyclopropane. 7 The 4-quinolone scaffold is a promising bioactive structure and exhibits superior qualities in the treatment of human disease. 8 For example, dorfloxacin, ciprofloxacin, and ofloxacin are widely used in varieties of acute and chronic bacterial infections.…”

Section: ■ Introductionmentioning

confidence: 99%

A Cascade Reaction of Michael Addition and Truce-Smiles Rearrangement to Synthesize Trisubstituted 4-Quinolone Derivatives

et al. 2020

View full text Add to dashboard Cite

A novel transition-metal-free cascade reaction to synthesize 4-quinolone derivatives has been demonstrated. Michael addition and Truce-Smiles rearrangement are included in this protocol, providing a broad scope of 4-quinolones in moderate-to-excellent yields. This work serves as an example of the use of sulfonamides through Truce−Smiles rearrangement to build heterocyclic compounds under mild conditions.

show abstract

A Stereoselective Arylative-Cyclopropanation Process

Cited by 21 publications

References 50 publications

Common Strategy for the Synthesis of Some Strychnos Indole Alkaloids

Common Strategy for the Synthesis of Some Strychnos Indole Alkaloids

Rapid Formation of Advanced Scaffolds from Phenols and Anilines

A Cascade Reaction of Michael Addition and Truce-Smiles Rearrangement to Synthesize Trisubstituted 4-Quinolone Derivatives

Contact Info

Product

Resources

About