Expanding the scope of the Babler–Dauben oxidation: 1,3-oxidative transposition of secondary allylic alcohols

Killoran, Patrick M.; Rossington, Steven B.; Wilkinson, James A.; Hadfield, John A.

doi:10.1016/j.tetlet.2016.07.076

Cited by 7 publications

(4 citation statements)

References 33 publications

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“…The product was prepared according to GP-I from the corresponding α,β-unsaturated alcohol (300.0 mg) to afford 1j (190.0 mg) as a white solid in 64% yield (step 3). Spectroscopic data are in good agreement with reported values …”

Section: Experimental Sectionsupporting

confidence: 90%

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Highly Enantioselective Synthesis of Functionalized Glutarimide Using Oxidative N-Heterocyclic Carbene Catalysis: A Formal Synthesis of (−)-Paroxetine

2019

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A simple yet highly effective approach toward enantioselective synthesis of trans-3,4-disubstituted glutarimides from readily available starting materials is developed using oxidative N-heterocyclic carbene catalysis. The catalytic reaction involves a formal [3 + 3] annulation between enals and substituted malonamides enabling the production of glutarimide derivatives in a single chemical operation via concomitant formation of C−C and C−N bonds. The reaction offers easy access to a broad range of functionalized glutarimides with excellent enantioselectivity and good yield. Synthetic application of the method is demonstrated via formal synthesis of (−)-paroxetine and other bioactive molecules.

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Section: Experimental Sectionsupporting

confidence: 90%

“…Spectroscopic data are in good agreement with reported values. 17 3-(1-Naphthalenyl)-2-propenal (1w). The product was prepared according to GP-I from the corresponding α,β-unsaturated alcohol (300.0 mg) to afford 1w (210.0 mg) as a white solid in 71% yield (step 3).…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

Highly Enantioselective Synthesis of Functionalized Glutarimide Using Oxidative N-Heterocyclic Carbene Catalysis: A Formal Synthesis of (−)-Paroxetine

2019

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“…In this regard, the compound 11 was treated with allylmagnesium bromide to deliver the corresponding hydroxy derivative 12 in 93 % yield. Then, the allyl Grignard product 12 was subjected to 1,3‐transposition with PCC (Babler‐Dauben oxidation) [61] to afford RRM precursor 13 (Scheme 1). When, 1.3 equivalents of PCC was used, compound 13 was isolated in 46 % yield along with 40 % of the recovered SM (Table 1; entry 1).…”

Section: Resultsmentioning

confidence: 99%

Synthetic Studies to exo‐Ring‐Junction based Fused 5/5/n‐Tricyclic Systems: Access to A, B, C‐Ring System of Longeracinphyllin A, Himalenine D, and Daphnipaxiamine A.

2023

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We report a short synthetic approach to various tricyclic systems that are present in several diquinane‐based natural products starting with a readily available exo‐dicyclopentadiene‐1‐one. To this end, we have successfully assembled a fused 5/5/7‐tricyclic enone via ring‐rearrangement metathesis as a key step. The strategy has been further extended to synthesize the 1,3‐dihydroxy and then 1‐keto‐3‐hydroxy derivatives by utilizing regio‐ and stereoselective epoxidation and ring‐rearrangement metathesis reactions as key steps. All these target compounds are found to be present in diquinane‐based natural products such as longeracinphyllins A, himalenine D and daphnipaxianine A, etc. Moreover, the newly synthesized tricyclic compounds matches the exact ring‐junction stereochemistry (5/5‐exo) of these natural products. Hence, the synthetic studies disclosed here may be useful in the synthesis of biologically significant natural products and in the drug design. The newly synthesized molecules were characterized by NMR and HRMS data. Some of these structures were confirmed by a single crystal X‐ray diffraction studies.

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“…A Grignard reaction of 12 using 2-methylallylmagnesium chloride gave allylic alcohol 13 , and its structure was established by X-ray crystallographic analysis. Pyridinium dichromate (PDC)-mediated oxidative rearrangement of allylic alcohol 13 afforded enone 14 in 86% yield over two steps. The next step was a selective reduction of the enone into a ketone in the presence of the terminal alkene moiety, which proved to be difficult because the terminal alkene was easily reduced under many reductive conditions.…”

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confidence: 99%

A Synthetic Route to The Core Structure of (−)-Retigeranic Acid A

Wang

Zhang

et al. 2021

Org. Lett.

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Retigeranic acid A is a uniquely structured pentacyclic sesterterpene bearing eight stereogenic centers. We report a concise route to the core structure of (−)-retigeranic acid A. The stereochemistry of its six chiral centers and three quaternary carbon centers was well-controlled. This route features two intramolecular Pauson–Khand reactions (IMPKRs): the first forged the D and E rings to deliver the triquinane subunit, and the second constructed the A and B rings and diastereoselectively installed the quaternary C6a center.

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Expanding the scope of the Babler–Dauben oxidation: 1,3-oxidative transposition of secondary allylic alcohols

Cited by 7 publications

References 33 publications

Highly Enantioselective Synthesis of Functionalized Glutarimide Using Oxidative N-Heterocyclic Carbene Catalysis: A Formal Synthesis of (−)-Paroxetine

Highly Enantioselective Synthesis of Functionalized Glutarimide Using Oxidative N-Heterocyclic Carbene Catalysis: A Formal Synthesis of (−)-Paroxetine

Synthetic Studies to exo‐Ring‐Junction based Fused 5/5/n‐Tricyclic Systems: Access to A, B, C‐Ring System of Longeracinphyllin A, Himalenine D, and Daphnipaxiamine A.

A Synthetic Route to The Core Structure of (−)-Retigeranic Acid A

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