120045-73-0Relevant academic research and scientific papers
The oxidative ring expansion of spiro-annulated chroman-4-ones: Syntheses of the rotenoid core and related benzoxanthones
Gabbutt, Christopher D.,Hepworth, John D.,Heron, B. Mark,Thomas, Jean-Luc
, p. 881 - 884 (2007/10/03)
Syntheses of dehydrorotenoid and benzoxanthone units from 2'-hydroxyacetophenone are described which feature a novel migration of spiro-substituted chroman-4-ones during their oxidative ring expansion. Conjugate reduction affords a trans B/C fused rotenoid and the related cis and trans fused tetrahydrobenzoxanthones.
Novel and Efficient Synthesis of Rotenoids via Intramolecular Radical Arylation
Ahmad-Junan, S. Asiah,Amos, Peter C.,Whiting, Donald A.
, p. 539 - 546 (2007/10/02)
Treatment of the iodoarylchromenes 22 with palladium acetate gave the tetracyclic compounds 23 via a formal but stereochemically disallowed Heck reaction; a crystalline intermediate palladium species 25 (X-ray analysis) was isolated.The method was employe
Rotenoid Synthesis via Radical Cyclisation
Ahmad-Junan, S. Asiah,Whiting, Donald A.
, p. 1160 - 1161 (2007/10/02)
The (+/-)-6aα, 12aα, 12α-chromanochromanol acetate (11; R=Ac), representing the core structure of the insecticidal rotenoid alcohol (2), has been synthesised in six steps from the chromone (4); the cis,cis-stereochemistry is obtained in an intramolecular 6-exo aryl radical addition.
