Rhodium-Catalyzed Enantioselective Decarboxylative Alkynylation of Allenes with Arylpropiolic Acids

Grugel, Christian P.; Breit, Bernhard

doi:10.1021/acs.orglett.7b04035

Cited by 52 publications

(16 citation statements)

References 53 publications

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“…The results implied that the absolute configuration of 2 was 2 S ,4 S ,5 R ,10 S ,3′ R ( Figure ). To confirm the above conclusion, the ester hydrolysis reaction for 2 was carried out, which furnished two hydrolysates, (3 R )- N -acetyl-β-phenylalanine ( 6 ) and a sesquiterpenoid ( 7 , named proversilin F), and their planar and absolute structures were confirmed by the single-crystal X-ray diffraction analyses (Figure ). Accordingly, the structure of 2 (2 S ,4 S ,5 R ,10 S ,3′ R ) was defined.…”

Section: Resultsmentioning

confidence: 99%

Proversilins A–E, Drimane-Type Sesquiterpenoids from the Endophytic Aspergillus versicolor

Zhang

Cao

et al. 2020

J. Nat. Prod.

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Five new drimane-type sesquiterpenoids, named proversilins A−E (1−5), were isolated from the endophytic fungus Aspergillus versicolor F210 isolated from the bulbs of Lycoris radiata. Their structures and absolute configurations were characterized by extensive spectroscopic analysis, including 1D and 2D NMR and HRESIMS data, comparison of experimental and calculated electronic circular dichroism data, and X-ray crystallography. Proversilins B−E (2−5) represent the first examples of natural products featuring an N-acetyl-β-phenylalanine moiety. Compounds 3 and 5 inhibited the growth of HL-60 cells with IC 50 values of 7.3 and 9.9 μM, respectively.

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Section: Resultsmentioning

confidence: 99%

Proversilins A–E, Drimane-Type Sesquiterpenoids from the Endophytic Aspergillus versicolor

Zhang

Cao

et al. 2020

J. Nat. Prod.

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“…Hydrofunctionalization of allenes mainly allowed the selective formation of C–N, C–O, and C–C bond. [ 2,3,5–8 ] The latter being performed through the addition of pronucleophiles such as malonates, [ 9–12 ] nitriles, [ 13–16 ] alkynes, [ 17–19 ] alkenes, [ 20–22 ] and aryl derivatives. The reaction of aromatic compounds with allenes, known as hydroarylation reaction, consists of adding an aryl moiety to a C–C double bond and constitutes a powerful tool to form a Csp 3 –Csp 2 bond in a regio‐ and stereoselective manner.…”

Section: Methodsmentioning

confidence: 99%

Hydroarylation of N‐Allenyl Derivatives Catalyzed by Copper**

et al. 2020

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An additive‐free copper catalytic system was used to perform the addition of (hetero)aryl nucleophiles to N‐allenyl derivatives. This intermolecular C–C bond formation occurs with both complete regio‐ and stereoselectivity to afford the linear (E) allylic product with moderate to excellent yields. This atom economical method is the first example of hydroarylation of allenes catalyzed by copper.

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“…Subsequently, HCl (1 mol/L, 150 μL) was added to obtain 4a and 5a. 23 To a stirred solution of compound 4a (9 mg) or 5a (8.8 mg) in CH 3 OH (100 μL)−toluene (350 μL) was added TMSCHN 2 (32 μL) in toluene (2 mol/L, 50 μL), the mixture was stirred for 30 min at room temperature. 24 Subsequently, the solution was removed in vacuo, and the residue was purified by semipreparative HPLC to obtain 4b (6.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

Amiaspochalasins A–H, Undescribed Aspochalasins with a C-21 Ester Carbonyl from Aspergillus micronesiensis

Zhang

Anbari

et al. 2019

J. Org. Chem.

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Amiaspochalasins A−H (1−8), eight undescribed aspochalasins, and trichalasin D (9), a known analogue, were isolated from the solid culture of Aspergillus micronesiensis. Compounds 1−9 are aspochalasins with a C-21 ester carbonyl, and their structures were determined by spectroscopic data, X-ray crystallographic analyses, electronic circular dichroism calculations, and chemical methods. The CH 3 -25 in compound 1 is located at C-16 rather than C-14 in the previously reported aspochalasins, endowing 1 with an unexpected carbon skeleton. Compounds 2 and 3 are the first examples of aspochalasins with an unprecedented 5/6/6/8 tetracyclic ring system. Compounds 4 and 5 are diastereomers of aspochalasins I and J, respectively. Compounds 6 and 7 are the first aspochalasins featuring a long open-chain system, and their absolute configurations were discussed by comparing the NMR data of the hydrolysis and methyl esterification products of 4 and 5. Compound 8 is an isomeride of 9. The cytotoxic and antimicrobial effects of 1−9 were tested.

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Rhodium-Catalyzed Enantioselective Decarboxylative Alkynylation of Allenes with Arylpropiolic Acids

Cited by 52 publications

References 53 publications

Proversilins A–E, Drimane-Type Sesquiterpenoids from the Endophytic Aspergillus versicolor

Proversilins A–E, Drimane-Type Sesquiterpenoids from the Endophytic Aspergillus versicolor

Hydroarylation of N‐Allenyl Derivatives Catalyzed by Copper**

Amiaspochalasins A–H, Undescribed Aspochalasins with a C-21 Ester Carbonyl from Aspergillus micronesiensis

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