SYNTHESIS OF ARISTOTELIA-TYPE ALKALOIDS .14. TOTAL SYNTHESIS OF (-ARISTOLONE())

Authors
DOBLER M BORSCHBERG HJ
Citation
M. Dobler et Hj. Borschberg, SYNTHESIS OF ARISTOTELIA-TYPE ALKALOIDS .14. TOTAL SYNTHESIS OF (-ARISTOLONE()), Tetrahedron : asymmetry, 5(10), 1994, pp. 2025-2032
Citations number
21
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
5
Issue
10
Year of publication
1994
Pages
2025 - 2032
Database
ISI
SICI code
0957-4166(1994)5:10<2025:SOAA.T>2.0.ZU;2-7
Abstract
The first total synthesis of the highly functionalized monoterpenoid i ndole alkaloid (+)-aristolone ((+)-2) is described. This investigation uncovered the hitherto unknown relative and absolute configuration of this rare metabolite which had been isolated before by others in ppm- amounts from Aristotelia australasica. Dehydration of synthetic (+)-2 led to a readily separable mixture of the two alkaloids 11,12-didehydr o-10-oxomakomakine ((+)-3) and 11,12-didehydro-10-oxohobartine ((-)-4) which had been isolated in 1988 from A. chilensis.