Synthesis of bicyclo[3.2.1]octanes by ring contraction

Kraus, George A.; Hon, Yung‐Son; Sy, James

doi:10.1021/jo00364a001

Cited by 8 publications

(2 citation statements)

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“…344 More recently, en route to the kaurane framework, a new exploitation of this methodology was proposed by Kraus and collaborators. 345 Ozonolysis of tetracyclic olefin 579 followed by cyclization of the resulting dialdehyde gave the [3.2.1] unit 580 found in corymbol diterpene. Also of interest is the remarkable formation of hydroxybicyclo[3.2.1]octane 583 by the base-mediated ring contraction of keto aldehyde 581 derived from naturally occurring swietenine.…”

Section: From Bridged Bicyclononane Precursorsmentioning

confidence: 99%

Synthesis of Functionalized Bicyclo[3.2.1]octanes and Their Multiple Uses in Organic Chemistry

1998

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Section: From Bridged Bicyclononane Precursorsmentioning

confidence: 99%

Synthesis of Functionalized Bicyclo[3.2.1]octanes and Their Multiple Uses in Organic Chemistry

1998

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“…One of the more interesting properties of the bicyclo[3.2.1]octane skeleton is its rigidity, which promotes specific coordination of two or more ligands on it, which can be of great value to medicinal chemists in the search for biological activity [14][15][16][17]. This structural moiety forms a basic framework of numerous biologically active natural compounds and their metabolites [18][19][20]. More importantly, compounds with the bicyclo[3.2.1]octene skeleton are proving to be potent inhibitors of dopamine and serotonin transporters and also play a crucial role in the treatment of central nervous system (CNS) disorders and AD [21,22].…”

Section: Introductionmentioning

confidence: 99%

Acetyl- and butyrylcholinesterase inhibitory activity of selected photochemicallysynthesized polycycles

Šagud¹,

Škorić²,

Vuk³

et al. 2019

Turk J Chem

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Alzheimer's disease (AD) is a progressive neurodegenerative disorder and the main cause of dementia in the elderly population. Since the treatment of AD has been associated with the activity of acetylcholinesterase (AChE) and butyrylcholinesterase (BChE), their inhibitors remain the main focus of AD investigations. In this study we evaluated cholinesterase inhibitory activity of 14 bicyclo[3.2.1]octene/octadiene derivatives and naturally occurring sesquiterpene alcohol cedrol. These 14 compounds have been efficiently and ecologically prepared by a photochemical approach in batch photochemical reactors. Various compounds with the bicyclo[3.2.1]octene skeleton have already been successfully evaluated for treatment of central nervous system disorders and AD. Among the tested polycyclic derivatives, compounds 4-[(9 S)-tricyclo[6.3.1.0 2,7 ]dodeca-2,4,6,10-tetraen-9-yl]pyridine (3) and (11 S)-11-(4-chlorophenyl)-12-[(E)-2-(4-chlorophenyl)ethenyl]tricyclo[6.3.1.0 2,7 ]dodeca-2,4,6,9-tetraene (6) showed the best inhibitory activity on BChE (IC 50 = 8.8 µ M) and AChE (IC 50 = 17.5 µ M), respectively.

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Stereo‐Controlled Synthesis of Vicinal Tertiary Carbinols: Application in the Synthesis of a Diol Substructure of Zaragozic Acid, Pactamycin and Ryanodol

Kim,

Puthukanoori,

Martha

et al. 2023

Chemistry A European J

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A novel and flexible approach for the stereo‐controlled synthesis of vicinal tertiary carbinols is reported. The developed strategy featured a highly diastereoselective singlet‐oxygen (O21) [4+2] cycloaddition of rationally designed cyclohexadienones (derived from oxidative dearomatization of the corresponding carboxylic‐acid appended phenol precursors), followed by programmed “O−O” and “C−C” bond cleavage. In doing so, a highly functionalized and versatile intermediate was identified and prepared in synthetically useful quantity as a plausible precursor to access a variety of designed and naturally occurring vicinal tertiary carbinol containing compounds. Most notably, the developed strategy was successfully applied in the stereo‐controlled synthesis of advanced core structures of zaragozic acid, pactamycin and ryanodol.

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Synthesis of bicyclo[3.2.1]octanes by ring contraction

Abstract: Two methods for the formation of the bicyclo[3.2.l]odane system by ring contraction of bicyclo[3.3.l]nonan-3-ones are described. One method uses the Biichi ring contraction. The other method uses the oxidative cleavage of an alkene followed by an aldol cyclization.

Cited by 8 publications

References 0 publications

Synthesis of Functionalized Bicyclo[3.2.1]octanes and Their Multiple Uses in Organic Chemistry

Synthesis of Functionalized Bicyclo[3.2.1]octanes and Their Multiple Uses in Organic Chemistry

Acetyl- and butyrylcholinesterase inhibitory activity of selected photochemicallysynthesized polycycles

Stereo‐Controlled Synthesis of Vicinal Tertiary Carbinols: Application in the Synthesis of a Diol Substructure of Zaragozic Acid, Pactamycin and Ryanodol

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