Enantioselective Total Synthesis of (−)‐Hosieine A

Ouyang, Jun; Yan, Rui; Mi, Xianwei; Hong, Ran

doi:10.1002/ange.201505251

Cited by 11 publications

(1 citation statement)

References 41 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…305 The major product of this reaction was the key starting material for the first total synthesis of (−)-hosieine A. 306 The transfer of the NC intermediate from the 9,10-DMA cycloadduct to other dienes is also used to prepare the HDA cycloadducts that serve for specific syntheses. This is the case represented in Scheme 161, where the 9,10-DMA cycloadducts of nitrosocarbonyls 1b, 1i, and 1w were submitted to thermolysis in the presence of the phosphono diene 320 to afford the cycloadduct 321 in 95% yield.…”

Section: Chemical Reviewsmentioning

confidence: 99%

Generation and Trapping of Nitrosocarbonyl Intermediates

Memeo

Quadrelli

2017

Chem. Rev.

View full text Add to dashboard Cite

The nitrosocarbonyls (R-CONO) are highly reactive species and remarkable intermediates toward different synthetic targets. This review will cover a research area whose impact in current organic synthesis is constantly increasing in the chemical community. This review represents the first and comprehensive picture on the generation and trapping of nitrosocarbonyls and is solidly built on more than 380 papers. Six different classes of key starting materials such as hydroxamic acids, N-hydroxy carbamates, N-hydroxyureas, nitrile oxides, and 1,2,4-oxadiazole-4-oxides were highlighted. The content of the review surveys all the methods to generate the nitrosocarbonyls through different approaches (oxidative, thermal, photochemical, catalytic, aerobic, and the less common ones) in the light of efficiency, yields, and mildness. The most successful trapping agents employed to catch these fleeting intermediates are reviewed, exploiting their superior dienophilic, enophilic, and electrophilic power. The work is completed by paragraphs dedicated to the detection of the intermediates, theoretical studies, and insights about the challenges and future directions for the field.

show abstract

Section: Chemical Reviewsmentioning

confidence: 99%

Generation and Trapping of Nitrosocarbonyl Intermediates

Memeo

Quadrelli

2017

Chem. Rev.

View full text Add to dashboard Cite

show abstract

Construction of Morphan Derivatives by Nitroso–Ene Cyclization: Mechanistic Insight and Total Synthesis of (±)‐Kopsone

et al. 2017

Self Cite

View full text Add to dashboard Cite

A type II nitroso–ene cyclization was developed for the construction of morphan derivatives with good functional‐group tolerance. DFT calculations revealed that the nitroso–ene reaction proceeds in a stepwise manner involving diradical or zwitterionic intermediates. The rate‐determining step is C−N bond formation, followed by a rapid hydrogen‐transfer step with a chair‐conformation transition state. The current approach was also successfully applied in the first total synthesis of (±)‐kopsone, a highly strained yet simple morphan‐type alkaloid isolated from Kopsia macrophylla.

show abstract

Total Synthesis of (+)‐ and (±)‐Hosieine A

2018

View full text Add to dashboard Cite

Described herein is ac oncise total synthesis of the highly potent nicotinic acetylcholine receptor ligand hosieine A in racemic and enantioenriched forms.T he synthesis requires only seven steps and features at elescoped reaction sequence initiated by ag old-catalyzed Rautenstrauchreaction.Supportinginformation and the ORCID identification number(s) for the author(s) of this article can be found under: https://doi.Scheme 2. Seven-step synthesis of (AE)-2.D CM = dichloromethane, LDA = lithium diisopropylamide, Tf = trifluoromethanesulfonyl, THF = tetrahydrofuran, TMS = trimethylsilyl.Scheme 3. Gold-catalyzed asymmetric Rautenstrauch reaction. EWG = electron-withdrawing group, Piv = pivaloyl.

show abstract

Enantioselective Total Synthesis of (−)‐Hosieine A

Cited by 11 publications

References 41 publications

Generation and Trapping of Nitrosocarbonyl Intermediates

Generation and Trapping of Nitrosocarbonyl Intermediates

Construction of Morphan Derivatives by Nitroso–Ene Cyclization: Mechanistic Insight and Total Synthesis of (±)‐Kopsone

Total Synthesis of (+)‐ and (±)‐Hosieine A

Contact Info

Product

Resources

About