177980-54-0Relevant academic research and scientific papers
BF3-Induced Rearrangement of Aziridinocyclopropanes Derived from 2-Phenylsulfonyl-1,3-Dienes. A New Approach to the Tropane Alkaloid Skeleton
Loeftroem, Claes M. G.,Baeckvall, Jan-E.
, p. 3371 - 3374 (1996)
Five N-substituted derivatives of 1,2-methylene-3,4-aziridino 2-phenylsulfonyl cycloalkanes (3a-e) were prepared from their corresponding epoxy cyclopropanes via ring opening of the epoxide by sodium azide and subsequent triphenlphosphine induced cyclization.BF3-induced reaction of compounds 3a-e resulted in a rearrangement via a cyclopropyl carbinyl cation intermediate.In the case of tosylaziridine 3c bicyclic product 5, (tropane skeleton), was formed as the major product.With carbamate derivative 3a exclusive rearrangement to fluorocycloheptene 7 took place.
BF3-induced rearrangement of aziridino cyclopropanes derived from 2-phenylsulfonyl 1,3-dienes. Application to the total synthesis of (±)-ferruginine
Jonsson,Loefstroem,Baeckvall
, p. 8454 - 8457 (2007/10/03)
Total synthesis of the alkaloid (±)-ferruginine (1) has been developed via the 2-phenylsulfonyl 1,3-diene approach. BF3-induced rearrangement of the N-protected cyclohexane aziridino cyclopropane 8, derived from its corresponding epoxy cyclopropane, afforded the desired tropane alkaloid skeleton 9 in good yield. Michael addition of nitroethane (as an acyl anion equivalent) and transformation of the nitro group of the adduct 10 to a keto function gave 11. Elimination of benzenesulfinic acid and subsequent replacement of the tosyl group by a methyl group afforded the title compound 1.
