BF3-induced rearrangement of aziridino cyclopropanes derived from 2-phenylsulfonyl 1,3-dienes. Application to the total synthesis of (+/-)-ferruginine

Authors
Jonsson, SY Lofstrom, CMG Backvall, JE
Citation
Sy. Jonsson et al., BF3-induced rearrangement of aziridino cyclopropanes derived from 2-phenylsulfonyl 1,3-dienes. Application to the total synthesis of (+/-)-ferruginine, J ORG CHEM, 65(25), 2000, pp. 8454-8457
Citations number
45
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
00223263 → ACNP
Volume
65
Issue
25
Year of publication
2000
Pages
8454 - 8457
Database
ISI
SICI code
0022-3263(200012)65:25<8454:BROACD>2.0.ZU;2-Q
Abstract
Total synthesis of the alkaloid(+/-)-ferruginine (I) 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 correspo nding 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.