Chemoselective ring construction from unsymmetrical 1,6-dienes via radical addition of sulfonyl halides

Riggi, Innocenzo De; Gastaldi, Stéphane; Surzur, Jean‐Marie; Bertrand, M. P.; Virgili, Albert

doi:10.1021/jo00049a014

Cited by 53 publications

(21 citation statements)

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“…The reaction was observed for the first time during an attempt to form a cyclopentane derivative through chlorosulfonylation of alkyne 1 a with para ‐toluenesulfonyl chloride and dilauroyl peroxide (DLP) in cyclohexane at reflux (Scheme ). In contrast to previously reported radical cascades involving the cyclization of dienes, and enynes or ring opening of vinylcyclopropanes, no trace of the expected cyclic chlorinated sulfone 3 a was observed. Instead, cyclic compound 2 a resulting from hydrosulfonylation was obtained in 66 % yield.…”

Section: Methodscontrasting

confidence: 99%

Hydrosulfonylation Reaction with Arenesulfonyl Chlorides and Tetrahydrofuran: Conversion of Terminal Alkynes into Cyclopentylmethyl Sulfones

2017

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An efficient and simple radical chain reaction to convert terminal alkynes into arenesulfonylmethylcyclopentanes is described. The reaction involves a radical addition-translocation-cyclization process and necessitates solely the use of readily available arenesulfonyl chlorides in tetrahydrofuran. Interestingly, this radical-mediated C-H activation process took place with a high level of retention of configuration when an enantiomerically pure starting material was used.

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Section: Methodscontrasting

confidence: 99%

Hydrosulfonylation Reaction with Arenesulfonyl Chlorides and Tetrahydrofuran: Conversion of Terminal Alkynes into Cyclopentylmethyl Sulfones

2017

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“…To a solution of triethyl pent-4-ene-1,2,2-tricarboxylate 44 (5 g, 16 mmol) in EtOH (20 mL) was added 1 N NaOH (19.2 mL, 19.2 mmol) at room temperature. The resulting mixture was stirred for 4 h before it was acidified with 2 N HCl.…”

Section: Methodsmentioning

confidence: 99%

Total synthesis and structure–activity relationship study of the potent cAMP signaling agonist (−)-alotaketal A

et al. 2013

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A detailed account of the first total synthesis of alotaketal A, a tricyclic spiroketal sesterterpenoid that potently activates the cAMP signaling pathway, is provided. The synthesis employs both intra- and intermolecular reductive allylation of esters for assembling one of the fragments and their coupling. A Hg(OAc)2-mediated allylic mercuration is used to introduce the C22-hydroxyl group. The subtle influence of substituents over the course of the spiroketalization process is revealed. The synthesis confirms the relative and absolute stereochemistry of (-)-alotaketal A and allows verification of alotaketal A’s effect over cAMP signaling using reporter-based FRET imaging assays with HEK 293T cells. Our studies also revealed alotaketal A’s unique activity in selectively targeting nuclear PKA signaling in living cells.

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“…For related literature, see: Fairlamb (2004); Hu et al (2003); Park & Hoffmann (1990); Otero & Cantero (1995); Riggi et al (1992).…”

Section: Related Literaturementioning

confidence: 99%

N-Benzyl-N-(4-chlorophenyl)acrylamide

Zhang

Wang

et al. 2007

Acta Cryst E

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In the molecular structure of the title compound, C16H14ClNO, the acrylamide unit is essentially planar and makes dihedral angles of 80.06 (12) and 68.91 (13)°, respectively, with the benzene and phenyl rings. The dihedral angle between the two rings is 49.79 (11)°. In the crystal structure, molecules are connected via weak C—H⋯O and C—H⋯π interactions, forming a molecular tape running along the b axis.

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Chemoselective ring construction from unsymmetrical 1,6-dienes via radical addition of sulfonyl halides

Cited by 53 publications

References 0 publications

Hydrosulfonylation Reaction with Arenesulfonyl Chlorides and Tetrahydrofuran: Conversion of Terminal Alkynes into Cyclopentylmethyl Sulfones

Hydrosulfonylation Reaction with Arenesulfonyl Chlorides and Tetrahydrofuran: Conversion of Terminal Alkynes into Cyclopentylmethyl Sulfones

Total synthesis and structure–activity relationship study of the potent cAMP signaling agonist (−)-alotaketal A

N-Benzyl-N-(4-chlorophenyl)acrylamide

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