Alkali metal-liquid ammonia reduction of γ-lactones to diols and cyclic hemiacetals: stereochemical influence by the neighbouring group on the nature

Chkraborty, Asit K.; Saha, Bijali; Ray, Chhanda; Ghatak, Usha Ranjan

doi:10.1016/s0040-4020(01)90319-9

Cited by 5 publications

(1 citation statement)

References 9 publications

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“…The formation of 4 from (-)- 3a via metal ammonia mediated chemo- and regio-selective hydrogenolysis 17, 18 (Scheme 2) further corroborated the stereo-preference in the Prins reaction of benzaldehyde and (+)-isopulegol as (1 S ,3 S ,6 S ,7 S ,9 S )-octahydro chromenol. 19…”

Section: Resultsmentioning

confidence: 55%

One-step, stereoselective synthesis of octahydrochromanes via the Prins reaction and their cannabinoid activities

Slater

Lasonkar

Haider

et al. 2018

Tetrahedron Letters

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Novel, functionalized octahydrochromene derivatives were synthesized in a single step the Prins reaction. Enantiomerically pure (+)-isopulegol was reacted with benzaldehyde to stereoselectively yield the corresponding octahydro-2-chromen-4-ol derivative containing five stereocenters. A total of 10 compounds were synthesized by altering the enantiomer of isopulegol and the substituted benzaldehyde, and the resulting enantiopure octahydrochromenes were screened against the cannabinoid receptor isoforms CB1 and CB2. Compounds containing an olefin at the C4 position [(+)-, (-)-, (-)-, (-)- and (-)-] of the octahydrochromene scaffold were found to exhibit reasonable displacement of [H] CP55,940 from the CB receptors, whereas the corresponding hydroxy analogs [(+)-, (+)-, (-)-, (-)- and (+)-] had very little or no effect.

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Section: Resultsmentioning

confidence: 55%