NMR ASSIGNMENTS AND ABSOLUTE STEREOCHEMISTRY OF 2 GUAIANOLIDE SESQUITERPENES FROM TANACETUM-DENSUM SUBSP AMANI

Authors
ULUBELEN A GOREN N JIANG TY SCOTT L TIANASOARAMOMOJY M SNYDER JK
Citation
A. Ulubelen et al., NMR ASSIGNMENTS AND ABSOLUTE STEREOCHEMISTRY OF 2 GUAIANOLIDE SESQUITERPENES FROM TANACETUM-DENSUM SUBSP AMANI, Magnetic resonance in chemistry, 33(11), 1995, pp. 900-904
Citations number
33
Categorie Soggetti
Spectroscopy,Chemistry
Journal title
Magnetic resonance in chemistry → ACNP
ISSN journal
07491581
Volume
33
Issue
11
Year of publication
1995
Pages
900 - 904
Database
ISI
SICI code
0749-1581(1995)33:11<900:NAAASO>2.0.ZU;2-7
Abstract
The guaianolide sesquiterpene pyrethroidinin (1) and the corresponding ketone parishin A (2) were isolated from Tanacetum densum subsp, aman i (Asteraceae). The absolute stereochemistry of 1 was established as ( 1R, 3R, 6S, 7S, 10R) on the basis of the differential shielding in the H-1 NMR spectra of the (-)- and (+)-O-methylmandelate esters. The str ucture, including absolute stereochemistry, of 2 was confirmed by oxid ation of 1 with Jones' reagent.