Abstract
Scutellaria subvelutina was found to be an excellent source of the
catalpol ester scutellarioside I (3) and this was chemically
converted into 5,7-bisdeoxycynanchoside. The partially protected
iridoid glucosides,
8,10:4’,6’-di-O-isopropylidene-5,7-bisdeoxycynanchoside (6) and
,3’,6’-tetra-O-benzoylantirrhinoside (10), as well as the fully
protected
5,6-O-isopropylidene-2’,3’,4’,6’-tetra-O-acetylantirrhinoside (8a)
were subjected to ozonolysis with reductive work-up using sodium
borohydride. Using a large excess of reductant, the reaction
mixtures from 6 and 8a were reduced completely to give the
respective polysubstituted cyclopentanols, while reduction of the
ozonolysis product from 10 could be stopped at the hemiacetal 11
by employing a smaller amount of reductant.
Original language | English |
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Journal | European Journal of Organic Chemistry |
Pages (from-to) | 365-370 |
ISSN | 1434-193X |
Publication status | Published - 1998 |