Chemistry of secologanin. Part 3. Graph analysis of the acidic deglycosylation of secologanin derivatives

DOI: 10.1016/S0040-4020(97)00659-5

Source and publish data:

Tetrahedron p. 10489 - 10502 (1997)

Update date:2022-07-30

Topics:

Authors:

Schwartz, Angela

Szabo, Laszlo F.

Podanyi, Benjamin

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Article abstract of DOI:10.1016/S0040-4020(97)00659-5

Acidic deglycosylation of N-methylbakankosine 02 and its 8,10-dihydro derivative 03 gave a rearranged 08a-b and an epimerized 09a-b pair of aglycones, respectively. It could be demonstrated that the thermodynamically controlled complex reaction sequence involved in the 'natural' series (02) 48 aglycones, 92 equilibria and 368 elementary steps, in the 'dihydro' series (03) 24 aglycones, 40 equilibria and 160 elementary steps. However, the shortest and most probable reaction sequence could be prognosed by graph analysis.

Full text of DOI:10.1016/S0040-4020(97)00659-5

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