One-step .alpha.-tosyloxylation of ketones with [hydroxy(tosyloxy)iodo]benzene

Koser, Gerald F.; Relenyi, Attila G.; Kalos, Alexander N.; Rebrovic, Louis; Wettach, Richard H.

doi:10.1021/jo00133a053

Cited by 234 publications

(100 citation statements)

References 3 publications

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“…Koser's reagent [20] [PhI(OH)(OTs)] was found to be superior to that of Davis' reagent (PhCHONSO 2 Ph) [21] (no reaction) and dimethyldioxirane [22] (mixture of regioisomers) in that only the desired regioisomer (i.e. 29) was obtained, albeit in moderate yield (47 %) (Scheme 6).…”

Section: Introductionmentioning

confidence: 99%

Towards the Total Synthesis of Vibsanin E, 15‐O‐Methylcyclovibsanin B,3‐Hydroxyvibsanin E, Furanovibsanin A, and 3‐O‐Methylfuranovibsanin A

et al. 2006

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Studies detailing synthetic approaches to a variety of biosynthetically related vibsanin‐type diterpenes (i.e. vibsanin E, 15‐O‐methylcyclovibsanin B, 3‐hydroxy‐vibsanin E, furanovibsanin A, and 3‐O‐methylfuranovibsanin A) are discussed. Biogenetically modelled approaches are coupled with an investigation of classical and modern six‐ to seven‐membered ring‐expansion protocols, which gain access to the central core of these natural products. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)

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Section: Introductionmentioning

confidence: 99%

Towards the Total Synthesis of Vibsanin E, 15‐O‐Methylcyclovibsanin B,3‐Hydroxyvibsanin E, Furanovibsanin A, and 3‐O‐Methylfuranovibsanin A

et al. 2006

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“…A solution of ester 5 14 (1 g, 2.76 mmol) and thioacetamide (0.31 g, 4.14 mmol) in DMF (10 mL) was stirred at 60 o C for 24 h (48 h for 11). After reaching rt, EtOAc (20 mL) was added and washed with H 2 O (3x10 mL).…”

Section: Typical Procedures For the Hantzsch Cyclization Synthesis Ofmentioning

confidence: 99%

Novel applications of the hypervalent iodine chemistry. Synthesis of thiazolo-fused quinolinones

Herrero¹,

Tellitu²,

Hernández³

et al. 2002

Arkivoc

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A synthesis of thiazolo [5,4-c]quinolinone derivatives featuring the use of two different hypervalent iodine reagents has been achieved starting from ethyl benzoylacetate in an efficient way. Hydroxy(tosyloxy)phenyliodine (HITB, Koser´s reagent) has been employed to functionalize the starting β-ketoester 4, and phenyliodine(III)bis(trifluoroacetate) (PIFA) to perform a ring closure reaction on the corresponding N-methoxyamides 9 and 14.

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“…The preparation of 2-mesyloxy- 23 and 2-tosyloxyketones 24 is already described but up to now, no method was available for the preparation of 2-mesyloxy-and 2-tosyloxyaldehydes. Attempts to prepare 2-tosyloxyhexadecanal by direct reaction of n-hexadecanal with HTIB 25 only led to complex reaction mixtures.…”

Section: Synthesis Of 2-mesyloxyhexadecanal [10]mentioning

confidence: 99%

“…for 2 h after which the solution was filtered and the filtrate washed successively with an aqueous 0.1 N sodium thiosulfate solution (until discoloration) and an aqueous saturated KI solution. The organic phase was dried, evaporated in vacuo and the resulting residue submitted to flash chromatography on silica gel (hexane/diethylether 8:2) affording 212 mg of 2-iodohexadecanal (56%) as an oil n-Hexadecanal methyl acetal [24]. To 100 mg (0.416 mmol; 1 eq.)…”

Section: -Iodohexadecanal [1]mentioning

confidence: 99%

Synthesis of Analogues of 2-iodohexadecanal, a Regulator of Iodine Metabolism in the Thyroid Gland

Bergen¹,

Daloze²,

Braekman³

1999

J. Braz. Chem. Soc.

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Com o objetivo futuro de fazer um estudo da relação estrutura-atividade, foram sintetisados vários derivados do 2-iodo-hexadecanal [1], um regulador do metabolismo de iodo na glândula tireóide, que diferem no comprimento da cadeia, natureza do substituinte e grupo funcional terminal.With the object of performing a structure-activity relationship study, we have synthesized several analogues of 2-iodohexadecanal [1], a regulator of iodine metabolism in the thyroid gland, differing by the chain length, the nature of the substituent, and/or the terminal functional group.

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One-step .alpha.-tosyloxylation of ketones with [hydroxy(tosyloxy)iodo]benzene

Cited by 234 publications

References 3 publications

Towards the Total Synthesis of Vibsanin E, 15‐O‐Methylcyclovibsanin B,3‐Hydroxyvibsanin E, Furanovibsanin A, and 3‐O‐Methylfuranovibsanin A

Towards the Total Synthesis of Vibsanin E, 15‐O‐Methylcyclovibsanin B,3‐Hydroxyvibsanin E, Furanovibsanin A, and 3‐O‐Methylfuranovibsanin A

Novel applications of the hypervalent iodine chemistry. Synthesis of thiazolo-fused quinolinones

Synthesis of Analogues of 2-iodohexadecanal, a Regulator of Iodine Metabolism in the Thyroid Gland

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