A total synthesis of sarcandralactone A: a general, concise, RCM enabled approach to lindenanolide sesquiterpenoids

Ramesh, Subburethinam; Mehta, Goverdhan

doi:10.1016/j.tetlet.2015.04.132

Cited by 20 publications

(3 citation statements)

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“…On the other hand, Mehta and Ramesh applied the present method exquisitely for the total syntheses of a series of lindenane-type sesquiterpenoids [22] and atractylenolide-type The reactions using m-bromoacetophenone (2c) and m-bromopropiophenone (2d) with 1 successfully afforded the corresponding 2(5H)-furanones 4c and 4d. In addition, 2(5H)-furanone 4e bearing p-TsO-group as the related cross-coupling leaving group was also produced.…”

Section: Resultsmentioning

confidence: 99%

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Straightforward Synthesis of 2(5H)-Furanones as Promising Cross-Coupling Partners: Direct Furanone Annulation Utilizing Ti-Mediated Aldol Addition

Ban

Ashida

Nakatsuji

et al. 2016

Molbank

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Direct 2(5H)-furanone annulation produces promising cross-coupling partners incorporating m-or p-bromo-and p-tosyloxyphenyl groups into the 5-position of a notable 2(5H)-furanone pharmacore. The present one-pot annulation method involves two distinctive reactions: (i) a powerful and crossed Ti-direct aldol addition and (ii) an acid-induced characteristic cyclocondensation, leading to 2(5H)-furanones. Suzuki-Miyaura cross-coupling of 5-(4-bromophenyl)-furan-2(5H)-ones, 5-(4-tosyloxyphenyl)-3,4-dimethylfuran-2(5H)-ones and a furan derivative successfully afforded the corresponding products with the 2(5H)-furanone skeleton.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Straightforward Synthesis of 2(5H)-Furanones as Promising Cross-Coupling Partners: Direct Furanone Annulation Utilizing Ti-Mediated Aldol Addition

Ban

Ashida

Nakatsuji

et al. 2016

Molbank

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“…183 Mehta's group also reported the construction of the key intermediate with a 5/6 bicyclic system by RCM reaction and using Simmons–Smith cyclopropanation as the key step to achieve the synthesis of a series of LSs. 184 Besides the 5/6-bicyclc precursor, Peng's group developed a bionic transformation strategy using a Wieland–Miescher ketone with a 6/6-bicyclc skeleton as the starting material. The key step involved S N 2-type intramolecular nucleophilic substitution to construct the cis , trans -3/5/6 tricyclic skeleton ( 360 ), 185 together with a wittig reaction or silyl migration and lactonization to build the unsaturated lactone ring of dienophile ( 361 ) and diene ( 362 ) (Scheme 11).…”

Section: Synthesis Of Lssmentioning

confidence: 99%

Chemistry and bioactivity of lindenane sesquiterpenoids and their oligomers

Luo,

Zhang,

Tang

et al. 2024

Nat. Prod. Rep.

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The J ulia– K ocienski 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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A total synthesis of sarcandralactone A: a general, concise, RCM enabled approach to lindenanolide sesquiterpenoids

Cited by 20 publications

References 36 publications

Straightforward Synthesis of 2(5H)-Furanones as Promising Cross-Coupling Partners: Direct Furanone Annulation Utilizing Ti-Mediated Aldol Addition

Straightforward Synthesis of 2(5H)-Furanones as Promising Cross-Coupling Partners: Direct Furanone Annulation Utilizing Ti-Mediated Aldol Addition

Chemistry and bioactivity of lindenane sesquiterpenoids and their oligomers

The J ulia– K ocienski Olefination

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