Stereoselective synthesis of C17–C34 fragment of antascomicin A

Vakiti, Jithender Reddy; Ghosh, Subhash

doi:10.1016/j.tetlet.2014.09.124

Cited by 4 publications

(2 citation statements)

References 33 publications

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“…For this reason, antascomicins are expected to be used as potential drug candidates for the treatment of neurodegenerative disorders. 87 Vakiti et al reported the facile synthesis of the C17-C34 88 The main steps in their synthetic scheme involved Sharpless asymmetric epoxidation, regioselective epoxide opening reaction via Gilman reagent, and Julia olenation reaction. In the rst step, the epoxy alcohol 185 (aer TBSOTf protection) was allowed to react with vinyl magnesium bromide and copper iodide in THF to acquire homoallylic alcohol 186 in 94% yield.…”

Section: Synthesis Of Macrolide-based Natural Productsmentioning

confidence: 99%

Gilman reagent toward the synthesis of natural products

Munir,

Zahoor,

Nazeer

et al. 2023

RSC Adv.

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Section: Synthesis Of Macrolide-based Natural Productsmentioning

confidence: 99%

Gilman reagent toward the synthesis of natural products

Munir,

Zahoor,

Nazeer

et al. 2023

RSC Adv.

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“…H derivatives [692], gamahonolide A [693], bitungolides [694], anamarine [695], cryptomoscatones D1 and D2 [696,697], an antascomicin A fragment [698], hyptolide [699], and rugulactone derivatives [700]; (6) γ,δ-unsaturated six-membered ring lactones, including those employed in syntheses of an altrose derivative [701];…”

Section: )mentioning

confidence: 99%

The chemistry of the carbon-transition metal double and triple bond: Annual survey covering the year 2014

Herndon

2016

Coordination Chemistry Reviews

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TheJulia–Kocienski Olefination

Blakemore¹,

Sephton

Ciganek

2018

Organic Reactions

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The Julia–Kocienski olefination is a direct connective synthesis of alkenes via the addition of metalated aryl alkyl sulfones to carbonyl compounds. The activating aromatic group associated with the sulfone must possess electrophilic character, and alkene formation occurs via β‐alkoxy sulfone formation, transfer of the aryl group from sulfur to oxygen via a Smiles rearrangement, and then elimination of sulfur dioxide and an aryloxide anion from the resulting β‐aryloxy sulfinate anion. The olefination process itself and the methods used to prepare the requisite sulfone substrates are tolerant of a wide variety of functional groups, and a variety of alkene targets can be prepared. Stereoselectivity is dependent on the nature of the sulfone, the carbonyl compound, the activating aryl moiety, and the reaction conditions. This chapter describes theoretical and operational aspects of the Julia–Kocienski olefination such that the reader will be able to obtain optimal results in his/her own research. A detailed mechanistic overview is included to account for the factors that influence stereoselectivity and yield. Methods for introducing sulfone activators into fragments of interest, best practices for generating sulfone anions, and optimal strategies for targeting different classes of alkene targets are discussed. Functional group compatibilities, reaction variants, and a comparison to other methods of alkene synthesis are also presented. Tabular surveys are organized according to type of alkene synthesized, with an emphasis on the degree of substitution and the level of conjugation about the newly formed double bond. The literature is covered from the initial disclosure of the Julia–Kocienski olefination in 1991 to the first quarter of 2016.

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Stereoselective synthesis of C17–C34 fragment of antascomicin A

Cited by 4 publications

References 33 publications

Gilman reagent toward the synthesis of natural products

Gilman reagent toward the synthesis of natural products

The chemistry of the carbon-transition metal double and triple bond: Annual survey covering the year 2014

TheJulia–Kocienski Olefination

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