ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The structure of the bisindole alkaloid amataine (= grandifoline, subsessiline)Amataine (1) was isolated from the roots of Hedranthera barteri (HOOK. F.) PICHON (Apocynaceae). In comparison to the alkaloid vobtusine (5), which was isolated from the same plant, 1 contains two hydrogen atoms less. By reduction of 1 with H2/PtO2 or with NaBH4 dihydromataine ( = isovobtusine, 13) was formed which is isomeric to 5. Acid catalysed water addition to 1 afforded hydratoamataine (15), which was reduced to 5 with NaBH4. Thermolysis of 15 gave 1. The difference between the two isomeric bases 5 and 13 has to be attributed to a different configuration at the spirocenter C(7). In contrast to 5 amataine (1) contains an ether bridge instead of a hydroxy group; this bridge is located between C (2′) and C (8).
Additional Material:
1 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19770600836
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