Total synthesis of the macrolide, (R,S)-zearalanone

Hurd, Richard N.; Shah, D. H.

doi:10.1021/jm00263a030

Cited by 12 publications

(3 citation statements)

References 5 publications

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“…( 2 ) .-To a solution of 5'-O-trityluridine ( 1 ) (2.12 g, 4 mmolI in a mixture of D M F (4 ml) and acetone (4 ml) were added benzyl chloride (0.58 ml, 5 mmol) and anhydrous potassium carbonate (0.78 g, 5.6 mmol). The nmr spectra were recorded with a J N M C-60 HL (CDCh) and Varian HA-100 spectrometer (DMSO-&), TMS being used as an internal standard.…”

Section: Methodsmentioning

confidence: 99%

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Elimination reactions on the di- and trimesylated derivatives of N3-benzyluridine

Sasaki¹,

Minamoto²,

Suzuki³

1973

J. Org. Chem.

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To investigate the base-catalyzed elimination reactions on multiply mesylated pyrimidine ribonucleosides, N8protected uridine derivatives, 3-benzyl-2',3'-di-O-mesyluridine (7) and 3-benzyl-235'-tri-O-mesyluridine (8), were synthesized as model compounds, which would be less likely to undergo cyclonucleoside formation. Sodium benzoate catalyzed elimination reaction on 7 and 8 gave the 2'-uridinenes, 9 and 17, with a mesyloxy group at Ci', which were converted to the crystalline 2'-uridinenes, 10 and 11. Treatment of 10 with potassium carbonate gave a new class of compound, endo-3-(3-benzyluracil-l-yl)-2-oxabicyclo[3.1.0]-4-oxocyclohexane (13). 8 with sodium acetate and sodium iodide gave 5'-substituted compounds, 18 and 19, respectively. 8 with potassium carbonate gave 2',3'-epoxy nucleoside (20) and 13. This suggests the intervention of two synchronous reaction paths.

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Section: Methodsmentioning

confidence: 99%

“…Thus, 5'-O-t'rityluridine (1) (Scheme I) with a slight excess of benzyl chloride and potassium carbonate gave exclusively 3-benzyl-5'-O-trityluridine (2) after 3-hr reflux in a mixture containing equal amounts of acetone and DhIF. For the present purpose, it was necessary to find better reaction conditions for the selective S3-benzylat'ion.…”

mentioning

confidence: 99%

Elimination reactions on the di- and trimesylated derivatives of N3-benzyluridine

Sasaki¹,

Minamoto²,

Suzuki³

1973

J. Org. Chem.

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“…Then, Corey et al [85] used new methods for activating carboxylic acids to form lactones with alcohols in remarkably improved yields. The formation of the macrocycle at the position of the ketone group using an internal Dieckmann condensation or an intramolecular alkylation of a protected cyanohydrin was proposed by Hurd [86] and Tsuji [87] , respectively. A study reporting formation of the macrolide via a 14-endo-trig cyclization from an allylic radical intermediate was reported in 1990 [88] .…”

Section: Chemical Synthesismentioning

confidence: 99%

Recent progress regarding the bioactivities, biosynthesis and synthesis of naturally occurring resorcinolic macrolides

Jiang

Zhang

et al. 2014

Acta Pharmacol Sin

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Macrolides, which comprise a family of lactones with different ring sizes, belong to the polyketide class of natural products. Resorcinolic macrolides, an important subgroup, possess interesting structures and exhibit a wide variety of bioactivities, such as anti-tumor, anti-bacteria, and anti-malaria activities, etc. This review summarizes progress in isolation, bioactivity studies, biosynthesis, and representative chemical syntheses of this group of macrolides in recent decades, encompassing 63 naturally occurring macrolides published in 120 articles.

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