Tandem Prins Cyclization for the Stereoselective Synthesis of the 4,5‐Diaryl‐hexahydropyrano[3,4‐<i>c</i>]chromene Skeleton of Calyxins I and J

Reddy, B. V. Subba; Mittapalli, Ramana R.; Reddy, S. Gopal; Sridhar, B.; Kumar, S. Kiran

doi:10.1002/ejoc.201500117

Cited by 15 publications

(3 citation statements)

References 26 publications

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“…Among them, the integrated Prins cyclization [9][10], in which the Prins cyclization and another type of reactions have been combined, is one of the most widely explored transformations in organic synthesis [11][12][13][14]. For instance, Reddy and co-workers have extensively studied the tandem cyclization involving Prins cyclization so far [15][16][17][18][19][20][21][22]. Scheme 1.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of halogenated bicyclic molecules involving Prins cyclization from aldehydes and non-conjugated diene alcohol

Matsumoto¹,

Ohtsuka²,

Hasebe³

et al. 2021

Preprint

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The reactions of aldehydes and a non-conjugated alcohol, (E)-octa-3,7-dien-1-ol, in the presence of halogen-containing reagents afforded the corresponding halogenated bicyclic molecules in good yields. The optimization, scope and limitations of the reactions as well as scale-up reactions have been examined. Quantum chemical calculations helped clarify the microscopic mechanism of a key reaction process, the introduction of a Cl atom to a bicyclic carbocation.

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Section: Introductionmentioning

confidence: 99%

Synthesis of halogenated bicyclic molecules involving Prins cyclization from aldehydes and non-conjugated diene alcohol

Matsumoto¹,

Ohtsuka²,

Hasebe³

et al. 2021

Preprint

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“…Synthesis of isoxazoles: 0.002 mol of chalcone derivatives reacted with equimolar hydroxylamine hydrochloride and sodium acetate in 25 mL ethanol and refluxed for 6 h. The mixture was concentrated and poured into crushed ice and stirred well to obtain the precipitate [6][7][8][9][10]. The precipitate obtained was filtered, washed and recrystallized.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization and Biological Evaluation of Isoxazoles Derived from 3-Aminoacetophenone

Kumar¹,

Kumar²,

Srinivasan

2019

Asian J. Chem.

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Isoxazoles were synthesized by condensing different aldehydes with 3-aminoacetophenone coupled to N-methyl piperazines. All the compounds were screened for anticancer activity against human breast cancer cell lines- MCF-7 and MDA-MB-468. The antimycobacterial activity of compounds were assessed against M. tuberculosis using microplate alamar blue assay (MABA). The structures of newly synthesized compounds established on the basis of their m.p., TLC, FTIR, mass and 1H NMR data. The results of antimycobacterial and anticancer studies shows that some of it posses mild to moderate activity against standard. These new synthesized compounds were identified and characterized, demonstrated antitubercular, in vivo efficacy in tumor models like MCF-7 and MDA-MB-468.

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“…When propanal was used as the electrophile, a 9:1 mixture of epimers 15 at C-5 was formed in 95% yield. Reddy and co-workers have very recently published their investigations on a similar cyclization . However, they reported the reaction of either 10 with 2,3,4-trifluorobenzaldehyde or the corresponding PMB protected phenol with a series of aldehydes, in the presence of TMSOTf at −40 °C, gave a mixture of products in varying yields …”

mentioning

confidence: 97%

Synthesis of Diarylheptanoid Scaffolds Inspired by Calyxins I and J

Ackrill

Sparkes²,

Willis³

2015

Org. Lett.

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γ,δ-Unsaturated alcohols are prepared efficiently in two steps from o-hydroxycinnamaldehyde. The TMSOTf-mediated reaction of the γ,δ-unsaturated alcohols with aldehydes creates two oxygen heterocycles and three new stereocenters in a single pot. The approach is versatile, and by varying the boronic acid, Grignard reagent, and aldehyde, different substituents may be introduced, while use of a chiral base in the conjugate addition gives enantioenriched products.

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Tandem Prins Cyclization for the Stereoselective Synthesis of the 4,5‐Diaryl‐hexahydropyrano[3,4‐c]chromene Skeleton of Calyxins I and J

Cited by 15 publications

References 26 publications

Synthesis of halogenated bicyclic molecules involving Prins cyclization from aldehydes and non-conjugated diene alcohol

Synthesis of halogenated bicyclic molecules involving Prins cyclization from aldehydes and non-conjugated diene alcohol

Synthesis, Characterization and Biological Evaluation of Isoxazoles Derived from 3-Aminoacetophenone

Synthesis of Diarylheptanoid Scaffolds Inspired by Calyxins I and J

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