ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Isolation of 14-Hydroxytaxodione from Plectranthus grandidentatus GÜRKE and of Seven New Dimeric Diterpenoids from P. grandidentatus, P. myrianthus and Coleus carnosus Structures of Grandidone A, 7-Epi-A, B, C, D and 7-Epi-DFrom the leaf-glands of the title plant the following abietane diterpenes have been isolated and their structures established by chemical, spectroscopical and X-ray methods: 14-hydroxytaxodione (5, 0,57%), new as a natural product, the already known coleons U (6, 0,17%) and V (7, 0,024%), and furthermore 7 novel dimeric compounds named grandidones (ca. 0,09%), Both grandidone A (1a) and 7-epigrandidone A (1b) as well as grandidone B (2a) and 7-epigrandidone B (2b) are C(7) acetals of 6, 7-Dioxoroyleanone with catecholes such as coleon U (→ 1a, 1b) or coleon V (→ 2a, 2b). Based on the relative configuration at C(7) of 1a which was established by X-ray analysis, the constitutions of 1b, 2a and 2b were assigned by HPLC. - controlled interconversions. The unstable grandidone C (3) is a C(7)-C(7′) linked bis-6-oxoroyleanone with C2-symmetry. Grandidone D (4a) and 7-epigrandidone D (4b) are spiro-dihydrofurans formed from 3 via a hypothetical bis (14-hydroxytaxodione) by intramolecular addition of HO-C(14) or HO-C(14′) to C(7′) to C(7′) or C(7). The relative configuration of 4a was established by X-ray analysis of its diacetate 4c. The absolute configuration of all dimers was established by the partial syntheses from 14-hydroxytaxodion (5) (entirely described in the following communication).
Additional Material:
10 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19810640729
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