Tetrahedron p. 1949 - 1954 (1987)
Update date:2022-08-04
Topics:
Jensen, Soren Rosendal
Kirk, Ole
Nilsen, Bent Juhl
The Vilsmeier reaction was utilized for the introduction of C-11 into iridoid glucosides, Aucubin hexaacetate (3a). 6,10-dideoxy aucubin tetraacetate (6a) and 8(S)-6,10-dideoxy-7,8-dihydro aucubin tetraacetate (7a) were used as substrates for the reaction. 6a and 7a were prepared by catalytic transfer hydrogenation of 3a with formic acid and Pd/C.The Vilsmeier reaction conditions were optimized with regard to the economic use of <(13)CHO>--DMF in the synthesis of <11-13C>-iridotrialglucoside (9).Remarcably, 5percent of the label in the product turned out to be situated at C-3.
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Doi:10.1016/S0040-4039(01)93725-6
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(2020)Doi:10.1080/00397911.2012.669874
(2013)Doi:10.1246/cl.1987.1153
(1987)Doi:10.1021/acscatal.6b00311
(2016)Doi:10.1016/j.bmcl.2007.09.030
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