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NMR assignments and absolute stereochemistry of two guaianolide sesquiterpenes from Tanacetum densume subsp. amani

✍ Scribed by Ayhan Ulubelen; Nezhun Gören; Tian-Yi Jiang; Lincoln Scott; Manoelson Tianasoa-Ramomojy; John M. K. Snyder


Publisher
John Wiley and Sons
Year
1995
Tongue
English
Weight
429 KB
Volume
33
Category
Article
ISSN
0749-1581

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✦ Synopsis


Abstract

The guaianolide sesquiterpene pyrethroidinin (1) and the corresponding ketone parishin A (2) wee isolated from Tanacetum densum subsp. amani (Asteraceae). The absolute stereochemistry of 1 was established as (1__R__, 3__R__, 6__S__, 7__S__, 10__R__) on the basis of the differential shielfing in the ^1^H NMR spectra of the (−)‐ and (+)‐O‐methylmandelate esters. The structure, including absolute stereochemistry, of 2 was confirmed by oxidation of 1 whit Jones' reagent.