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

1995    ULUBELEN, A; GOREN, N; JIANG, TY; SCOTT, L; TIANASOARAMOMOJY, M; SNYDER, JK

The guaianolide sesquiterpene pyrethroidinin (1) and the corresponding ketone parishin A (2) were isolated from Tanacetum densum subsp, amani (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 structure, including absolute stereochemistry, of 2 was confirmed by oxidation of 1 with Jones' reagent.