Total Syntheses of Aflavazole and 14-Hydroxyaflavinine

Li, Hailong; Chen, Qi-Feng; Lu, Zhaohong; Li, Ang

doi:10.1021/jacs.6b10880

Cited by 79 publications

(43 citation statements)

References 81 publications

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“…9 We expected that 6 could be produced from aromatic compound 7 through the diastereoselective 1,2addition of lithium compound 8. The tetrasubstituted benzene ring, [27][28][29][30] the most critical synthetic challenge in 7, could be prepared from 9 through a series of functional group manipulations, including a chemoselective cleavage of the C10-O bond and aromatization cascade. In turn, the tetracyclic core in 9 with the desired stereochemistry at C3 was anticipated to be synthesized from 10, using the Achmatowicz reaction followed by type I intramolecular [5 + 2] cycloaddition with exo selectivity.…”

Section: Resultsmentioning

confidence: 99%

Asymmetric Total Synthesis of Phomarol

Fan

Wang

et al. 2021

CCS Chem

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The first and asymmetric total synthesis of phomarol, an uncommon C25 steroid, is described. The synthetically challenging benzocycloheptane motif, found in phomarol and some other naturally occurring molecules, was synthesized efficiently using a very mild acid-promoted type I [5 + 2] cycloaddition, followed by regio-and chemoselective cleavage of the C-O bond and aromatization cascade. This work is the first example of using the hydrogen bonding between the hydroxy group and oxidopyrylium ylide to control the stereoselectivity of cycloadditions. The highly functionalized tetrahydropyran ring of phomarol was produced efficiently based on our suggested biomimetic pathway.

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Section: Resultsmentioning

confidence: 99%

Asymmetric Total Synthesis of Phomarol

Fan

Wang

et al. 2021

CCS Chem

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“…C-Sn bond is called a kind of very significant carbon–metal bond, which has many applications in organic chemistry, medicinal chemistry, and biological chemistry [96] , [97] , [98] .…”

Section: Applications Of Ultrasound In the Total Synthesis Of Bioactive Natural Productsmentioning

confidence: 99%

Applications of ultrasound in total synthesis of bioactive natural products: A promising green tool

Majhi¹

2021

Ultrasonics Sonochemistry

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“…Li and co-workers demonstrated an elegant total synthesis of aflavazole (71), which capitalized upon an AlI 3promoted alkynyl Prins cyclization. 36 Conditions for the synthesis of Prins substrate 70 from -ethoxy acetal 69 are described in Table 4.…”

Section: Alkynyl Prins Cyclizations In Natural Product Synthesismentioning

confidence: 99%

Alkynyl Prins and Alkynyl Aza-Prins Annulations: Scope and Synthetic Applications

Abdul-Rashed¹,

Holt²,

Frontier³

2020

Synthesis

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This review focuses on alkynyl Prins and alkynyl aza-Prins cyclization processes, which involve intramolecular coupling of an alkyne with either an oxocarbenium or iminium electrophile. The oxocarbenium or iminium species can be generated through condensation- or elimination-type processes, to achieve an overall bimolecular annulation that enables the synthesis of both oxygen- and nitrogen-containing saturated heterocycles with different ring sizes and substitution patterns. Also discussed are cascade processes in which alkynyl Prins heterocyclic adducts react to trigger subsequent pericyclic reactions, including [4+2] cycloadditions and Nazarov electrocyclizations, to rapidly construct complex small molecules. Finally, examples of the use of alkynyl Prins and alkynyl aza-Prins reactions in the synthesis of natural products are described. The review covers the literature through the end of 2019.1 Introduction1.1 Alkyne-Carbonyl Coupling Pathways1.2 Coupling/Cyclization Cascades Using the Alkynyl Prins Reaction2 Alkynyl Prins Annulation (Oxocarbenium Electrophiles)2.1 Early Work2.2 Halide as Terminal Nucleophile2.3 Oxygen as Terminal Nucleophile2.4 Arene as Terminal Nucleophile (Intermolecular)2.5 Arene Terminal Nucleophile (Intramolecular)2.6 Cyclizations Terminated by Elimination3 Synthetic Utility of Alkynyl Prins Annulation3.1 Alkynyl Prins-Mediated Synthesis of Dienes for a [4+2] Cyclo- addition-Oxidation Sequence3.2 Alkynyl Prins Cyclization Adducts as Nazarov Cyclization Precursors3.3 Alkynyl Prins Cyclization in Natural Product Synthesis4 Alkynyl Aza-Prins Annulation4.1 Iminium Electrophiles4.2 Activated Iminium Electrophiles5 Alkynyl Aza-Prins Cyclizations in Natural Product Synthesis6 Summary and Outlook

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Total Syntheses of Aflavazole and 14-Hydroxyaflavinine

Cited by 79 publications

References 81 publications

Asymmetric Total Synthesis of Phomarol

Asymmetric Total Synthesis of Phomarol

Applications of ultrasound in total synthesis of bioactive natural products: A promising green tool

Alkynyl Prins and Alkynyl Aza-Prins Annulations: Scope and Synthetic Applications

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