Z-1-vinyliodide durch Wittig-reaktion

Bestmann, Hans Jürgen; Rippel, Hans Christoph; Dostalek, Roman

doi:10.1016/s0040-4039(01)93757-8

Cited by 59 publications

(15 citation statements)

References 5 publications

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“…The Wittig reaction of aldehyde 26 with the ylide derived from phosphonium salt 34 under Stork conditions17 gave the desired cis ‐alkene 32 as an inseparable mixture with trans ‐alkene 35 , an unidentifiable impurity, and diiodo‐substituted alkene 36 , a side product which has previously been reported (see Scheme ) 18. The assignments of these structures were tentatively determined by 1 H NMR spectroscopic analysis of the crude mixture.…”

Section: Resultsmentioning

confidence: 67%

Synthetic Studies towards Radicicol through Biomimetic Macrolactonization and Transannular Aromatization Reactions

et al. 2014

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Studies towards the total synthesis of the natural product radicicol are described that employ a late‐stage esterification and aromatization by trapping a ketene intermediate. The subsequent biomimetic aromatization of the resultant triketo ester gave highly functionalized resorcylates. Two distinct methods were examined that trap the ketene intermediate through either an intermolecular or intramolecular process. In the first approach, the synthesis of the resorcylate was followed by a ring‐closing metathesis, which gave the macrolactone and protected precursors to monocillin I. In the second approach, an intramolecular ketene trapping was examined as an alternative to close the macrocycle and form the resorcylate macrolactone. These studies showcased a wide range of sensitive functional groups that tolerated the aromatization reaction conditions, which started from the corresponding dioxinone precursors.

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Section: Resultsmentioning

confidence: 67%

Synthetic Studies towards Radicicol through Biomimetic Macrolactonization and Transannular Aromatization Reactions

et al. 2014

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“…Iodoalkenes can be prepared by a variety of methods. 13 This procedure uses the method of Brown involving conversion of a terminal alkyne to the corresponding 1-iodoalkyne, followed by a hydroboration-protonolysis to afford the terminal Z -1-iodoalkene. 14 We note that the preparation of Z -1-iodooctene presented here is modeled directly after the Denmark synthesis of Z -1-iodoheptene that appears in Volume 81 of Organic Syntheses .…”

Section: Discussionmentioning

confidence: 99%

Preparation of 1‐Monoacylglycerols via the Suzuki‐Miyaura Reaction: 2,3‐Dihydroxypropyl (Z)‐tetradec‐7‐enoate

et al. 2014

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(2,2‐Dimethyl‐1,3‐dioxolan‐4‐yl) methyl hexanoate 5‐Hexanoic acid 4‐(Dimethylamino)pyridine N,N ′‐Dicyclohexylcarboimide DL‐1,2‐sopropylidene glycerol 1‐Iodo‐1‐octyne Iodine n ‐Butyllithium ( Z)‐ 1‐Iodo‐1‐octene Borane dimethyl sulfide complex Cyclohexane (2,2‐Dimethyl‐1,3‐dioxolan‐4‐yl)methyl ( Z)‐ tetra‐7‐enolate 9‐Borabicyclo[3.3.1]none Cesium carbonate Triphenylarsine Dichlor[1,1′‐bis(diphenylphosphino)ferrocene]palladium(II),dichloromethne 2,3‐Dihydroxypropyl ( Z)‐ tetradec‐7‐enoate

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“…A similar observation has only been reported by the group of Bestmann. 48 To explain the generation of the unwanted diiodide, they suggested an iodine-hydrogen exchange process, as shown in Scheme 9.…”

Section: Methodsmentioning

confidence: 99%

Stereoselective Total Synthesis of Etnangien and Etnangien Methyl Ester

Arikan

et al. 2010

J. Org. Chem.

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ABSTRACT. A highly stereoselective joint total synthesis of the potent polyketide macrolide antibiotics etnangien and etnangien methyl ester was accomplished by a convergent strategy and proceeds in 23 steps (longest linear sequence). Notable synthetic features include a sequence of highly stereoselective substrate-controlled aldol reactions to set the characteristic assembly of methyl-and hydroxyl-bearing stereogenic centers of the propionate portions, an efficient diastereoselective Heck macrocyclization of a deliberately conformationally-biased precursor, and a late-stage introduction of the labile side chain by means of a high-yielding Stille coupling of protective-group free precursors.Along the way, an improved, reliable protocol for a Z-selective Stork-Zhao-Wittig olefination of aldehydes was developed and an effective protocol for a 1,3-syn reduction of sterically particularly hindered β-hydroxy ketones was devised. Within the synthetic campaign, a more detailed understanding of the intrinsic isomerisation pathways of these labile natural products was elaborated. The expedient and flexible strategy of the etnangiens should be amenable to designed analogues of these RNApolymerase inhibitors, thus enabling further exploration of the promising biological potential of these macrolide antibiotics.

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Z-1-vinyliodide durch Wittig-reaktion

Cited by 59 publications

References 5 publications

Synthetic Studies towards Radicicol through Biomimetic Macrolactonization and Transannular Aromatization Reactions

Synthetic Studies towards Radicicol through Biomimetic Macrolactonization and Transannular Aromatization Reactions

Preparation of 1‐Monoacylglycerols via the Suzuki‐Miyaura Reaction: 2,3‐Dihydroxypropyl (Z)‐tetradec‐7‐enoate

Stereoselective Total Synthesis of Etnangien and Etnangien Methyl Ester

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