ABSOLUTE STEREOCHEMISTRY OF THE PENTACYCLIC QUATERNARY INDOLE ALKALOID OPHIORRHIZINE - SYNTHETIC INCORPORATION OF CINCHOLOIPON ETHYL-ESTER INTO (-)-OPHIORRHIZINE

Authors
OHBA M SETO S FUJII T SARGENT MV ARBAIN D
Citation
M. Ohba et al., ABSOLUTE STEREOCHEMISTRY OF THE PENTACYCLIC QUATERNARY INDOLE ALKALOID OPHIORRHIZINE - SYNTHETIC INCORPORATION OF CINCHOLOIPON ETHYL-ESTER INTO (-)-OPHIORRHIZINE, Heterocycles, 38(8), 1994, pp. 1741-1744
Citations number
20
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Heterocycles → ACNP
ISSN journal
03855414
Volume
38
Issue
8
Year of publication
1994
Pages
1741 - 1744
Database
ISI
SICI code
0385-5414(1994)38:8<1741:ASOTPQ>2.0.ZU;2-K
Abstract
The absolute stereochemistry of the Ophiorrhiza alkaloid ophiorrhizine has been defined as shown in formula [(-)-1] by a chemical correlatio n with the Cinchona alkaloid cinchonine through cincholoipon ethyl est er [(+)-3] and the lactim ether [(+)-2]. The correlation was achieved by the chiral synthesis of ophiorrhizine [(-)-1] from (+)-2 via the in termediates [(+)-5], [(+)-7], [(+)-6], (8), [(-)-9}, [(-)10], (11), [( -)-12], and [(-)-13].